In organic chemistry, a thial or thioaldehyde is a functional group which is similar to an aldehyde, RC(O)H, in which a sulfur (S) atom replaces the oxygen (O) atom of the aldehyde (R represents an alkyl or aryl group). Thioaldehydes are even more reactive than thioketones. Unhindered thioaldehydes are generally too reactive to be isolated — for example, thioformaldehyde, H2C=S, condenses to the cyclic trimer 1,3,5-trithiane. Thioacrolein, H2C=CHCH=S, formed by decomposition of allicin from garlic, undergoes a self Diels-Alder reaction giving isomeric vinyldithiins.[1][2] While thioformaldehyde is highly reactive, it is found in interstellar space along with its mono- and di-deuterated isotopologues.[3] With sufficient steric bulk, however, stable thioaldehydes can be isolated.[4]
Chemical structure of a thial
In early work, the existence of thioaldehydes was inferred by trapping processes. For instance the reaction of Fc2P2S4 with benzaldehyde was proposed to form thiobenzaldehyde, which forms a cycloadduct with the dithiophosphine ylides to form a C2PS3 ring.[5]
Cooper, N.J. (2005). "Thioaldehydes and Thioketones". Comprehensive Organic Functional Group Transformations II. pp. 355–396. doi:10.1016/B0-08-044655-8/00053-2. ISBN978-0-08-044655-4.
Murai, Toshiaki (2018). "The Construction and Application of C=S Bonds". Topics in Current Chemistry. 376 (4): 31. doi:10.1007/s41061-018-0209-0. PMID 29987439. S2CID 51605664.
Referencesedit
^H. W. Kroto; B. M. Landsberg; R. J. Suffolk; A. Vodden (1974). "The photoelectron and microwave spectra of the unstable species thioacetaldehyde, CH 3CHS, and thioacetone, (CH 3) 2CS". Chemical Physics Letters. 29 (2): 265–269. Bibcode:1974CPL....29..265K. doi:10.1016/0009-2614(74)85029-3.
^E. Block (2010). Garlic and Other Alliums: The Lore and the Science. Royal Society of Chemistry. ISBN978-0-85404-190-9.
^N. Takeda; N. Tokitoh; R. Okazaki (1997). "Synthesis, Structure, and Reactions of the First Rotational Isomers of Stable Thiobenzaldehydes, 2,4,6-Tris[bis(trimethylsilyl)methyl]thiobenzaldehydes". Chemistry: A European Journal. 3: 62–69. doi:10.1002/chem.19970030111.
^A. Capperucci; A. Degl’Innocenti; P. Scafato; P. Spagnolo (1995). "Synthetic Applications of Bis(trimethylsilyl)sulfide: Part II. Synthesis of Aromatic and Heteroaromatic o-Azido-Thioaldehydes". Chemistry Letters. 24 (2): 147. doi:10.1246/cl.1995.147.
April 27, 2024
thial, organic, chemistry, thial, thioaldehyde, functional, group, which, similar, aldehyde, which, sulfur, atom, replaces, oxygen, atom, aldehyde, represents, alkyl, aryl, group, thioaldehydes, even, more, reactive, than, thioketones, unhindered, thioaldehyde. In organic chemistry a thial or thioaldehyde is a functional group which is similar to an aldehyde RC O H in which a sulfur S atom replaces the oxygen O atom of the aldehyde R represents an alkyl or aryl group Thioaldehydes are even more reactive than thioketones Unhindered thioaldehydes are generally too reactive to be isolated for example thioformaldehyde H2C S condenses to the cyclic trimer 1 3 5 trithiane Thioacrolein H2C CHCH S formed by decomposition of allicin from garlic undergoes a self Diels Alder reaction giving isomeric vinyldithiins 1 2 While thioformaldehyde is highly reactive it is found in interstellar space along with its mono and di deuterated isotopologues 3 With sufficient steric bulk however stable thioaldehydes can be isolated 4 Chemical structure of a thial In early work the existence of thioaldehydes was inferred by trapping processes For instance the reaction of Fc2P2S4 with benzaldehyde was proposed to form thiobenzaldehyde which forms a cycloadduct with the dithiophosphine ylides to form a C2PS3 ring 5 See also editThioketone Thioenol Organosulfur compoundsFurther reading editCooper N J 2005 Thioaldehydes and Thioketones Comprehensive Organic Functional Group Transformations II pp 355 396 doi 10 1016 B0 08 044655 8 00053 2 ISBN 978 0 08 044655 4 Murai Toshiaki 2018 The Construction and Application of C S Bonds Topics in Current Chemistry 376 4 31 doi 10 1007 s41061 018 0209 0 PMID 29987439 S2CID 51605664 References edit H W Kroto B M Landsberg R J Suffolk A Vodden 1974 The photoelectron and microwave spectra of the unstable species thioacetaldehyde CH 3CHS and thioacetone CH 3 2CS Chemical Physics Letters 29 2 265 269 Bibcode 1974CPL 29 265K doi 10 1016 0009 2614 74 85029 3 E Block 2010 Garlic and Other Alliums The Lore and the Science Royal Society of Chemistry ISBN 978 0 85404 190 9 CDMS N Takeda N Tokitoh R Okazaki 1997 Synthesis Structure and Reactions of the First Rotational Isomers of Stable Thiobenzaldehydes 2 4 6 Tris bis trimethylsilyl methyl thiobenzaldehydes Chemistry A European Journal 3 62 69 doi 10 1002 chem 19970030111 A Capperucci A Degl Innocenti P Scafato P Spagnolo 1995 Synthetic Applications of Bis trimethylsilyl sulfide Part II Synthesis of Aromatic and Heteroaromatic o Azido Thioaldehydes Chemistry Letters 24 2 147 doi 10 1246 cl 1995 147 Retrieved from https en wikipedia org w index php title Thial amp oldid 1199112565, wikipedia, wiki, book, books, library,
