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1,2-Dimethyldiborane

February 16, 2024

1,2-Dimethyldiborane is an organoboron compound with the formula [(CH3)BH2]2. Structurally, it is related to diborane, but with methyl groups replacing terminal hydrides on each boron. It is the dimer of methylborane, CH3BH2, the simplest alkylborane.[1] 1,2-Dimethyldiborane can exist in a cis- and a trans arrangement.[2] 1,2-Dimethyldiborane is an easily condensed, colorless gas that ignites spontaneously in air.

1,2-Dimethyldiborane

cis-1,2-Dimethyldiborane

trans-1,2-Dimethyldiborane
Names
Preferred IUPAC name
1,2-Dimethyldiborane(6)
Other names
Symmetrical dimethyldiborane
Identifiers
  • 17156-88-6 N
3D model (JSmol)
  • Interactive image
  • InChI=1S/C2H10B2/c1-3-5-4(2)6-3/h3-4H,1-2H3[1]
    Key: CMZSWMSJMMTTMF-UHFFFAOYSA-N[2]
  • C[BH]1[H][BH](C)[H]1
Properties
(CH3BH2)2
Molar mass 55.72 g mol−1
Appearance Colorless gas
Melting point −124.9 °C (−192.8 °F; 148.2 K)
Boiling point 4 °C (39 °F; 277 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is YN ?)

An isomer of 1,2-dimethyldiborane is 1,1-dimethyldiborane, known as unsymmetrical dimethyldiborane, which has two methyl groups on one boron atom. Other methylated versions of diborane including methyldiborane, trimethyldiborane, tetramethyldiborane. Trimethylborane exists as a monomer.

Preparation edit

Methylboranes were first prepared by H. I. Schlesinger and A. O. Walker in the 1930s.[3][4]

In a more modern synthesis, 1,2-dimethyldiborane is produced by treating lithium methylborohydride with hydrogen chloride:[1]

2 LiCH3BH3 + 2 HCl → (CH3BH2)2 + 2 H2 + 2 LiCl

Instead of hydrogen chloride, methyl iodide or trimethylsilyl chloride can be used.[5]

Lithium methylborohydride can be made by treating methylboronic esters with lithium aluminium hydride.[5]

Miscellaneous routes edit

Methylboranes arise the reaction of diborane and trimethylborane. This reaction produces 1-methyldiborane, 1,1-dimethyldiborane, 1,1,2-trimethyldiborane, and 1,1,2,2-tetramethyldiborane. By treating monomethyldiborane with ether, dimethyl ether borane (CH3)2O.BH3 leaving methylborane which rapidly dimerises to 1,2-dimethyldiborane.[6] The reaction is complex.

Tetramethyl lead reacts with diborane to give a range of methyl-substituted diboranes, ending up at trimethylborane, but including 1,1-dimethyldiborane, and trimethyldiborane. Other products are hydrogen gas and lead metal.[7]

Other methods to form methyldiboranes include treating hydrogen with trimethylborane between 80 and 200 °C under pressure, or treating a metal borohydride with trimethylborane in the presence of hydrogen chloride, aluminium chloride or boron trichloride. If the borohydride is sodium borohydride, then methane is a side product. If the metal is lithium, then no methane is produced.[3] dimethylchloroborane and methyldichloroborane are also produced as gaseous products.[3]

When Cp2Zr(CH3)2 reacts with diborane, a borohydro group inserts into the zirconium-carbon bond, and methyl diboranes are produced.[8]

In ether dimethylcalcium reacts with diborane to produce dimethyldiborane and calcium borohydride:[9]

Ca(CH3)2 + 2 B2H6 → Ca(BH4)2 + B2H4(CH3)2

1,2-Dimethyldiborane is produced by the room temperature disproportionation of trimethyldiborane.[10]

Physical and spectroscopic properties edit

cis-1,2-Dimethyldiborane melts at −132.5 °C; trans-1,2-dimethyldiborane melts at −102 °C.[11] The cis-1,2-dimethyldiborane molecule has point group Cs. A trans-1,2-dimethyldiborane molecule has point group C2. Unsymmetrical dimethyldiborane melts at −150.2 °C.[12] Vapour pressure is approximated by Log P = 7.363−(1212/T).[12] The vapour pressure for the symmetrical isomer is given by Log P = 7.523−(1290/T).[12]

Gas chromatography can be used to determine the amounts of the methyl boranes in a mixture. The order of elution are: diborane, monomethyldiborane, trimethylborane, 1,1-dimethyldiborane, 1,2-dimethyldiborane, trimethyldiborane, and last tetramethyldiborane.[13]

The nuclear resonance shift for the bridge hydrogen is 9.55 ppm for the unsymmetrical isomer and 9.73 ppm for the symmetrical isomers, compared to 10.49 for diborane.[14]

Reactions edit

Methylborane shows little tendency to disproportionate (redistribute) at room temperature. It reacts stepwise with alkenes to produce mono and dialkylmethylboranes. More methylated boranes are less stable.[5]

1,2-Dimethyldiborane slowly converts to 1,1-dimethyldiborane.[15]

Methylborane hydrolyzes to methylboronic acid:[6]

(MeBH2)2 + 4 H2O → CH3B(OH)2 + 4 H2

Symmetrical dimethyldiborane reacts with trimethylamine to yield a solid adduct trimethylamine-methylborane (CH3)3N·BH2CH3.[6]

When dimethyldiborane is combined with ammonia and heated, B-methyl borazoles are produced. These borazoles can have one, two or three methyl groups substituted on the boron atoms.[16][17]

Under normal conditions dimethyldiborane does not react with hydrogen.[18]

Related species edit

  • Lithium trihydromethylborate [CH3BH3]−.[5]
  • Isomers of diethyldiborane can be produced by analogous methods.[19]
  • 1,2- 2,2- and 2,4-dimethyltetraborane,[20] 1,2-dimethylpentaborane[21] 2,3-dimethylpentaborane,[22] 4,5-dimethylhexaborane,[23] and 5,6- 6,8- 6,9-dimethyldecaborane.[24]

References edit

  1. ^ a b Srebnik, Morris; Cole, Thomas E.; Brown, Herbert C. (January 1987). "Methylborane - a remarkable unhindered monoalkylborane which achieves the controlled sequential hydroboration of representative alkenes". Tetrahedron Letters. 28 (33): 3771–3774. doi:10.1016/s0040-4039(00)96380-9.
  2. ^ Low, M. J. D. (1968). "Characteristic Infrared Frequencies of Methyldiboranes". The Journal of Chemical Physics. 48 (5): 2386–2387. Bibcode:1968JChPh..48.2386L. doi:10.1063/1.1669454.
  3. ^ a b c Long, L. H.; Wallbridge, M. G. H. (1965). "646. The Chemistry of Boron. Part VI. New Preparative Methods and Decomposition Studies Relating to Methyldiboranes". Journal of the Chemical Society (Resumed): 3513–3520. doi:10.1039/JR9650003513. (subscription required)
  4. ^ Schlesinger, H. I.; Walker, A. O. (April 1935). "Hydrides of Boron. IV. The Methyl Derivatives of Diborane". Journal of the American Chemical Society. 57 (4): 621–625. doi:10.1021/ja01307a009.
  5. ^ a b c d Brown, Herbert C.; Cole, Thomas E.; Srebnik, Morris; Kim, Kee Won (December 1986). "Hydroboration. 79. Preparation and Properties of Methylborane and Dimethylborane and Their Characteristics as Hydroborating Sgents. Synthesis of Tertiary Alcohols Containing Methyl Groups via Hydroboration". The Journal of Organic Chemistry. 51 (25): 4925–4930. doi:10.1021/jo00375a031.
  6. ^ a b c Bell, R. P.; Emeléus, H. J. (1948). "The Boron Hydrides and Related Compounds". Quarterly Reviews, Chemical Society. 2 (2): 132. doi:10.1039/QR9480200132.
  7. ^ Holliday, A.K.; N. Jessop, G. (November 1967). "The Reaction of Tetramethyllead with Diborane". Journal of Organometallic Chemistry. 10 (2): 291–293. doi:10.1016/s0022-328x(00)93089-4.
  8. ^ Marsella, John A.; Caulton, Kenneth G. (May 1982). "Dealkylation of Zirconium(IV) by Borane: the Intimate Mechanism of an Alkyl Transfer Reaction". Journal of the American Chemical Society. 104 (9): 2361–2365. doi:10.1021/ja00373a005.
  9. ^ James, B. D.; Wallbridge, M. G. H. (1970). "Metal Tetrahydroborates". In Lippard, Stephen J. (ed.). Progress in Inorganic Chemistry, Volume 11. Wiley. p. 185. ISBN 0471-54081-1.
  10. ^ Lehmann, Walter J.; Wilson, Charles O.; Shapiro, I. (1961). "Infrared Spectra of Alkyldiboranes. V. Tri- and Tetramethyl- and Ethyldiboranes". The Journal of Chemical Physics. 34 (3): 783. Bibcode:1961JChPh..34..783L. doi:10.1063/1.1731675.
  11. ^ Hedberg, Lise; Hedberg, Kenneth; Kohler, David A.; Ritter, David M.; Schomaker, Verner (May 1980). "Electron-diffraction investigations of the molecular structures of cis- and trans-1,2-dimethyldiborane". Journal of the American Chemical Society. 102 (10): 3430–3434. doi:10.1021/ja00530a021.
  12. ^ a b c Onak, Thomas (1 January 1966). Stone, F. G. A.; West, Robert (eds.). Advances in Organometallic Chemistry. New York, London: Academic Press. p. 284. ISBN 9780080580043. Retrieved 14 August 2015.
  13. ^ Seely, G. R.; Oliver, J. P.; Ritter, D. M. (December 1959). "Gas-Liquid Chromatographic Analysis of Mixtures Containing Methyldiboranes". Analytical Chemistry. 31 (12): 1993–1995. doi:10.1021/ac60156a032.
  14. ^ Leach, John B.; Ungermann, Charles B.; Onak, Thomas P. (January 1972). "Proton magnetic resonance studies on methyl and chloro substituted diboranes". Journal of Magnetic Resonance. 6 (1): 74–83. Bibcode:1972JMagR...6...74L. doi:10.1016/0022-2364(72)90088-1.
  15. ^ Lehmann, Walter J.; Wilson, Charles O.; Shapiro, I. (1960). "Infrared Spectra of Alkyldiboranes. III. 1,2-Dimethyl- and 1,2-Diethyldiboranes". The Journal of Chemical Physics. 33 (2): 590. Bibcode:1960JChPh..33..590L. doi:10.1063/1.1731190.
  16. ^ Sheldon, J. C.; Smith, B. C. (1960). "The borazoles". Quarterly Reviews, Chemical Society. 14 (2): 202. doi:10.1039/QR9601400200.
  17. ^ Schlesinger, H. I.; Horvitz, Leo; Burg, A. B. (March 1936). "Hydrides of Boron. VI. The Action of Ammonia on the Methyl Diboranes". Journal of the American Chemical Society. 58 (3): 409–414. doi:10.1021/ja01294a008.
  18. ^ Adams, Roy M. (September 1959). "Organoboron Compounds" (PDF). Metal-Organic Compounds. Advances in Chemistry. Vol. 23. p. 92. doi:10.1021/ba-1959-0023.ch010. ISBN 0-8412-0024-6. Retrieved 17 August 2015.
  19. ^ Mikhailov, B. M. (April 1962). "The Chemistry Of Diborane". Russian Chemical Reviews. 31 (4): 209. Bibcode:1962RuCRv..31..207M. doi:10.1070/RC1962v031n04ABEH001281. S2CID 250909492.
  20. ^ Deever, William R.; Ritter, David M. (November 1969). "Methyltetraboranes. I. 2-Methyl and 1,2-, 2,2-, and 2,4-dimethyl derivatives". Inorganic Chemistry. 8 (11): 2461–2467. doi:10.1021/ic50081a043.
  21. ^ Addison, C. C.; Davidson, G. (1973). "Elements of Group III". Inorganic Chemistry of the Main-Group Elements. Vol. 1. p. 68. doi:10.1039/9781847556370-00053. ISBN 978-0-85186-752-6. (subscription required)
  22. ^ Onak, Thomas; Friedman, Lawrence B.; Hartsuck, Jean A.; Lipscomb, William N. (July 1966). "Rearrangement of 1,2- to 2,3-Dimethylpentaborane(9)". Journal of the American Chemical Society. 88 (14): 3439–3440. doi:10.1021/ja00966a051.
  23. ^ Shore, S. G. (1975). "Nido and Arachno Boron Hydrides". In Muetterties, Earl L (ed.). Boron Hydride Chemistry. Academic Press. p. 150. ISBN 0-12-509650-X.
  24. ^ Dunstan, I.; Williams, R. L.; Blay, N. J. (1960). "970. Boron hydride derivatives. Part V. Nucleophilic substitution in decaborane". Journal of the Chemical Society (IV): 5012–5015. doi:10.1039/JR9600005012. Retrieved 19 August 2015.

Extra reading edit

  • Carpenter, J. H.; Jones, W. J.; Jotham, R. W.; Long, L. H. (1968). "Laser-source Raman spectroscopy and the Raman spectra of the methyldiboranes". Chemical Communications (15): 881. doi:10.1039/C19680000881.
  • Lehmann, Walter J.; Wilson, Charles O.; Shapiro, I. (1960). "Infrared Spectra of Alkyldiboranes. I. Monomethyldiboranes". The Journal of Chemical Physics. 32 (4): 1088. Bibcode:1960JChPh..32.1088L. doi:10.1063/1.1730853.
  • Carpenter, J.H.; Jones, W.J.; Jotham, R.W.; Long, L.H. (June 1970). "The Raman spectra of the methyldiboranes—I 1, 1-dimethyldiborane and tetramethyldiborane". Spectrochimica Acta Part A: Molecular Spectroscopy. 26 (6): 1199–1214. Bibcode:1970AcSpA..26.1199C. doi:10.1016/0584-8539(70)80027-7.
  • Jungfleisch, Francis M. (1973). (Thesis). Ohio State University. Archived from the original on 4 March 2016. Retrieved 30 July 2015.
  • Isadore Shapiro; C. O. Wilson; J. F. Ditter; W. J. Lehmann (1961). Borax to Boranes (PDF). Advances in Chemistry Series. Vol. 32. American Chemical Society. pp. 134–136. doi:10.1021/ba-1961-0032.ch014. mass spectroscopy
  • Levison, K. A.; Perkins, P. G. (1970). "Methylaluminium compounds I. The Electronic Structure of Some Methylaluminium and Methylboron Hydrides". Theoretica Chimica Acta. 17 (1): 1–14. doi:10.1007/BF00526759. S2CID 198179226. charge distribution and atom location calculations

February 16, 2024
dimethyldiborane, organoboron, compound, with, formula, structurally, related, diborane, with, methyl, groups, replacing, terminal, hydrides, each, boron, dimer, methylborane, ch3bh2, simplest, alkylborane, exist, trans, arrangement, easily, condensed, colorle. 1 2 Dimethyldiborane is an organoboron compound with the formula CH3 BH2 2 Structurally it is related to diborane but with methyl groups replacing terminal hydrides on each boron It is the dimer of methylborane CH3BH2 the simplest alkylborane 1 1 2 Dimethyldiborane can exist in a cis and a trans arrangement 2 1 2 Dimethyldiborane is an easily condensed colorless gas that ignites spontaneously in air 1 2 Dimethyldiborane cis 1 2 Dimethyldiboranetrans 1 2 DimethyldiboraneNamesPreferred IUPAC name 1 2 Dimethyldiborane 6 Other names Symmetrical dimethyldiboraneIdentifiersCAS Number 17156 88 6 N3D model JSmol Interactive imageInChI InChI 1S C2H10B2 c1 3 5 4 2 6 3 h3 4H 1 2H3 1 Key CMZSWMSJMMTTMF UHFFFAOYSA N 2 SMILES C BH 1 H BH C H 1PropertiesChemical formula CH3BH2 2Molar mass 55 72 g mol 1Appearance Colorless gasMelting point 124 9 C 192 8 F 148 2 K Boiling point 4 C 39 F 277 K Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N what is Y N Infobox references An isomer of 1 2 dimethyldiborane is 1 1 dimethyldiborane known as unsymmetrical dimethyldiborane which has two methyl groups on one boron atom Other methylated versions of diborane including methyldiborane trimethyldiborane tetramethyldiborane Trimethylborane exists as a monomer Contents 1 Preparation 1 1 Miscellaneous routes 2 Physical and spectroscopic properties 3 Reactions 4 Related species 5 References 6 Extra readingPreparation editMethylboranes were first prepared by H I Schlesinger and A O Walker in the 1930s 3 4 In a more modern synthesis 1 2 dimethyldiborane is produced by treating lithium methylborohydride with hydrogen chloride 1 2 LiCH3BH3 2 HCl CH3BH2 2 2 H2 2 LiClInstead of hydrogen chloride methyl iodide or trimethylsilyl chloride can be used 5 Lithium methylborohydride can be made by treating methylboronic esters with lithium aluminium hydride 5 Miscellaneous routes edit Methylboranes arise the reaction of diborane and trimethylborane This reaction produces 1 methyldiborane 1 1 dimethyldiborane 1 1 2 trimethyldiborane and 1 1 2 2 tetramethyldiborane By treating monomethyldiborane with ether dimethyl ether borane CH3 2O BH3 leaving methylborane which rapidly dimerises to 1 2 dimethyldiborane 6 The reaction is complex Tetramethyl lead reacts with diborane to give a range of methyl substituted diboranes ending up at trimethylborane but including 1 1 dimethyldiborane and trimethyldiborane Other products are hydrogen gas and lead metal 7 Other methods to form methyldiboranes include treating hydrogen with trimethylborane between 80 and 200 C under pressure or treating a metal borohydride with trimethylborane in the presence of hydrogen chloride aluminium chloride or boron trichloride If the borohydride is sodium borohydride then methane is a side product If the metal is lithium then no methane is produced 3 dimethylchloroborane and methyldichloroborane are also produced as gaseous products 3 When Cp2Zr CH3 2 reacts with diborane a borohydro group inserts into the zirconium carbon bond and methyl diboranes are produced 8 In ether dimethylcalcium reacts with diborane to produce dimethyldiborane and calcium borohydride 9 Ca CH3 2 2 B2H6 Ca BH4 2 B2H4 CH3 21 2 Dimethyldiborane is produced by the room temperature disproportionation of trimethyldiborane 10 Physical and spectroscopic properties editcis 1 2 Dimethyldiborane melts at 132 5 C trans 1 2 dimethyldiborane melts at 102 C 11 The cis 1 2 dimethyldiborane molecule has point group Cs A trans 1 2 dimethyldiborane molecule has point group C2 Unsymmetrical dimethyldiborane melts at 150 2 C 12 Vapour pressure is approximated by Log P 7 363 1212 T 12 The vapour pressure for the symmetrical isomer is given by Log P 7 523 1290 T 12 Gas chromatography can be used to determine the amounts of the methyl boranes in a mixture The order of elution are diborane monomethyldiborane trimethylborane 1 1 dimethyldiborane 1 2 dimethyldiborane trimethyldiborane and last tetramethyldiborane 13 The nuclear resonance shift for the bridge hydrogen is 9 55 ppm for the unsymmetrical isomer and 9 73 ppm for the symmetrical isomers compared to 10 49 for diborane 14 Reactions editMethylborane shows little tendency to disproportionate redistribute at room temperature It reacts stepwise with alkenes to produce mono and dialkylmethylboranes More methylated boranes are less stable 5 1 2 Dimethyldiborane slowly converts to 1 1 dimethyldiborane 15 Methylborane hydrolyzes to methylboronic acid 6 MeBH2 2 4 H2O CH3B OH 2 4 H2Symmetrical dimethyldiborane reacts with trimethylamine to yield a solid adduct trimethylamine methylborane CH3 3N BH2CH3 6 When dimethyldiborane is combined with ammonia and heated B methyl borazoles are produced These borazoles can have one two or three methyl groups substituted on the boron atoms 16 17 Under normal conditions dimethyldiborane does not react with hydrogen 18 Related species editLithium trihydromethylborate CH3BH3 5 Isomers of diethyldiborane can be produced by analogous methods 19 1 2 2 2 and 2 4 dimethyltetraborane 20 1 2 dimethylpentaborane 21 2 3 dimethylpentaborane 22 4 5 dimethylhexaborane 23 and 5 6 6 8 6 9 dimethyldecaborane 24 References edit a b Srebnik Morris Cole Thomas E Brown Herbert C January 1987 Methylborane a remarkable unhindered monoalkylborane which achieves the controlled sequential hydroboration of representative alkenes Tetrahedron Letters 28 33 3771 3774 doi 10 1016 s0040 4039 00 96380 9 Low M J D 1968 Characteristic Infrared Frequencies of Methyldiboranes The Journal of Chemical Physics 48 5 2386 2387 Bibcode 1968JChPh 48 2386L doi 10 1063 1 1669454 a b c Long L H Wallbridge M G H 1965 646 The Chemistry of Boron Part VI New Preparative Methods and Decomposition Studies Relating to Methyldiboranes Journal of the Chemical Society Resumed 3513 3520 doi 10 1039 JR9650003513 subscription required Schlesinger H I Walker A O April 1935 Hydrides of Boron IV The Methyl Derivatives of Diborane Journal of the American Chemical Society 57 4 621 625 doi 10 1021 ja01307a009 a b c d Brown Herbert C Cole Thomas E Srebnik Morris Kim Kee Won December 1986 Hydroboration 79 Preparation and Properties of Methylborane and Dimethylborane and Their Characteristics as Hydroborating Sgents Synthesis of Tertiary Alcohols Containing Methyl Groups via Hydroboration The Journal of Organic Chemistry 51 25 4925 4930 doi 10 1021 jo00375a031 a b c Bell R P Emeleus H J 1948 The Boron Hydrides and Related Compounds Quarterly Reviews Chemical Society 2 2 132 doi 10 1039 QR9480200132 Holliday A K N Jessop G November 1967 The Reaction of Tetramethyllead with Diborane Journal of Organometallic Chemistry 10 2 291 293 doi 10 1016 s0022 328x 00 93089 4 Marsella John A Caulton Kenneth G May 1982 Dealkylation of Zirconium IV by Borane the Intimate Mechanism of an Alkyl Transfer Reaction Journal of the American Chemical Society 104 9 2361 2365 doi 10 1021 ja00373a005 James B D Wallbridge M G H 1970 Metal Tetrahydroborates In Lippard Stephen J ed Progress in Inorganic Chemistry Volume 11 Wiley p 185 ISBN 0471 54081 1 Lehmann Walter J Wilson Charles O Shapiro I 1961 Infrared Spectra of Alkyldiboranes V Tri and Tetramethyl and Ethyldiboranes The Journal of Chemical Physics 34 3 783 Bibcode 1961JChPh 34 783L doi 10 1063 1 1731675 Hedberg Lise Hedberg Kenneth Kohler David A Ritter David M Schomaker Verner May 1980 Electron diffraction investigations of the molecular structures of cis and trans 1 2 dimethyldiborane Journal of the American Chemical Society 102 10 3430 3434 doi 10 1021 ja00530a021 a b c Onak Thomas 1 January 1966 Stone F G A West Robert eds Advances in Organometallic Chemistry New York London Academic Press p 284 ISBN 9780080580043 Retrieved 14 August 2015 Seely G R Oliver J P Ritter D M December 1959 Gas Liquid Chromatographic Analysis of Mixtures Containing Methyldiboranes Analytical Chemistry 31 12 1993 1995 doi 10 1021 ac60156a032 Leach John B Ungermann Charles B Onak Thomas P January 1972 Proton magnetic resonance studies on methyl and chloro substituted diboranes Journal of Magnetic Resonance 6 1 74 83 Bibcode 1972JMagR 6 74L doi 10 1016 0022 2364 72 90088 1 Lehmann Walter J Wilson Charles O Shapiro I 1960 Infrared Spectra of Alkyldiboranes III 1 2 Dimethyl and 1 2 Diethyldiboranes The Journal of Chemical Physics 33 2 590 Bibcode 1960JChPh 33 590L doi 10 1063 1 1731190 Sheldon J C Smith B C 1960 The borazoles Quarterly Reviews Chemical Society 14 2 202 doi 10 1039 QR9601400200 Schlesinger H I Horvitz Leo Burg A B March 1936 Hydrides of Boron VI The Action of Ammonia on the Methyl Diboranes Journal of the American Chemical Society 58 3 409 414 doi 10 1021 ja01294a008 Adams Roy M September 1959 Organoboron Compounds PDF Metal Organic Compounds Advances in Chemistry Vol 23 p 92 doi 10 1021 ba 1959 0023 ch010 ISBN 0 8412 0024 6 Retrieved 17 August 2015 Mikhailov B M April 1962 The Chemistry Of Diborane Russian Chemical Reviews 31 4 209 Bibcode 1962RuCRv 31 207M doi 10 1070 RC1962v031n04ABEH001281 S2CID 250909492 Deever William R Ritter David M November 1969 Methyltetraboranes I 2 Methyl and 1 2 2 2 and 2 4 dimethyl derivatives Inorganic Chemistry 8 11 2461 2467 doi 10 1021 ic50081a043 Addison C C Davidson G 1973 Elements of Group III Inorganic Chemistry of the Main Group Elements Vol 1 p 68 doi 10 1039 9781847556370 00053 ISBN 978 0 85186 752 6 subscription required Onak Thomas Friedman Lawrence B Hartsuck Jean A Lipscomb William N July 1966 Rearrangement of 1 2 to 2 3 Dimethylpentaborane 9 Journal of the American Chemical Society 88 14 3439 3440 doi 10 1021 ja00966a051 Shore S G 1975 Nido and Arachno Boron Hydrides In Muetterties Earl L ed Boron Hydride Chemistry Academic Press p 150 ISBN 0 12 509650 X Dunstan I Williams R L Blay N J 1960 970 Boron hydride derivatives Part V Nucleophilic substitution in decaborane Journal of the Chemical Society IV 5012 5015 doi 10 1039 JR9600005012 Retrieved 19 August 2015 Extra reading editCarpenter J H Jones W J Jotham R W Long L H 1968 Laser source Raman spectroscopy and the Raman spectra of the methyldiboranes Chemical Communications 15 881 doi 10 1039 C19680000881 Lehmann Walter J Wilson Charles O Shapiro I 1960 Infrared Spectra of Alkyldiboranes I Monomethyldiboranes The Journal of Chemical Physics 32 4 1088 Bibcode 1960JChPh 32 1088L doi 10 1063 1 1730853 Carpenter J H Jones W J Jotham R W Long L H June 1970 The Raman spectra of the methyldiboranes I 1 1 dimethyldiborane and tetramethyldiborane Spectrochimica Acta Part A Molecular Spectroscopy 26 6 1199 1214 Bibcode 1970AcSpA 26 1199C doi 10 1016 0584 8539 70 80027 7 Jungfleisch Francis M 1973 Reactions of Methyl Substituted Diboranes and 2 2 Dimethyltetraborane with Amine Bases Thesis Ohio State University Archived from the original on 4 March 2016 Retrieved 30 July 2015 Isadore Shapiro C O Wilson J F Ditter W J Lehmann 1961 Borax to Boranes PDF Advances in Chemistry Series Vol 32 American Chemical Society pp 134 136 doi 10 1021 ba 1961 0032 ch014 mass spectroscopy Levison K A Perkins P G 1970 Methylaluminium compounds I The Electronic Structure of Some Methylaluminium and Methylboron Hydrides Theoretica Chimica Acta 17 1 1 14 doi 10 1007 BF00526759 S2CID 198179226 charge distribution and atom location calculations Retrieved from https en wikipedia org w index php title 1 2 Dimethyldiborane amp oldid 1116576433, wikipedia, wiki, book, books, library,

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