In organic chemistry, paddlane is any member of a class of tricyclicsaturated hydrocarbons having two bridgehead carbon atoms joined by four bridges. The name derives from a supposed resemblance of the molecule to a paddle wheel: namely, the rings would be the propeller's blades, and the shared carbon atoms would be its axis.
General structure of [m.n.o.p]paddlane
Systematically named tricyclo [m.n.o.p1,m+2]alkanes,[1] these compounds have been referred to as [m.n.o.p]paddlanes. The notation [m.n.o.p]paddlane means the member of the family whose rings have m, n, o, and p carbons, not counting the two bridgeheads; or m + 2, n + 2, o + 2, and p + 2 carbons, counting them. The chemical formula is therefore C2+m+n+o+pH2(m+n+o+p). When p = 0, the compounds are propellanes.
Compoundsedit
[1.1.1.1]Paddlane
The best known paddlane is [1.1.1.1]paddlane which can be seen as a precursor to octahedrane (C6), an allotrope of elemental carbon.
The American chemist Philip Eaton, famous for being the first to synthesize the "impossible" cubane molecule, has conducted studies for the synthesis of [2.2.2.2]paddlane.[2] The first mention of paddlane goes back to 1973.[3]
^Eaton, Philip E.; Leipzig, Bernard D. (1983). "Toward tricyclo[2.2.2.2]decane. 1. [n.2.2.2]Paddlane systems, n = 10–14". Journal of the American Chemical Society. 105 (6): 1656. doi:10.1021/ja00344a042.
^Hahn, E. H.; Bohm, H.; Ginsburg, D. (1973). "The synthesis of paddlanes: Compounds in which quaternary bridgehead carbons are joined by four chains". Tetrahedron Letters. 14 (7): 507. doi:10.1016/S0040-4039(01)95684-9.
paddlane, organic, chemistry, paddlane, member, class, tricyclic, saturated, hydrocarbons, having, bridgehead, carbon, atoms, joined, four, bridges, name, derives, from, supposed, resemblance, molecule, paddle, wheel, namely, rings, would, propeller, blades, s. In organic chemistry paddlane is any member of a class of tricyclic saturated hydrocarbons having two bridgehead carbon atoms joined by four bridges The name derives from a supposed resemblance of the molecule to a paddle wheel namely the rings would be the propeller s blades and the shared carbon atoms would be its axis General structure of m n o p paddlane Systematically named tricyclo m n o p1 m 2 alkanes 1 these compounds have been referred to as m n o p paddlanes The notation m n o p paddlane means the member of the family whose rings have m n o and p carbons not counting the two bridgeheads or m 2 n 2 o 2 and p 2 carbons counting them The chemical formula is therefore C2 m n o pH2 m n o p When p 0 the compounds are propellanes Compounds edit nbsp 1 1 1 1 Paddlane The best known paddlane is 1 1 1 1 paddlane which can be seen as a precursor to octahedrane C6 an allotrope of elemental carbon The American chemist Philip Eaton famous for being the first to synthesize the impossible cubane molecule has conducted studies for the synthesis of 2 2 2 2 paddlane 2 The first mention of paddlane goes back to 1973 3 References edit IUPAC Compendium of Chemical Terminology 2nd ed the Gold Book 1997 Online corrected version 2006 paddlanes doi 10 1351 goldbook P04395 Eaton Philip E Leipzig Bernard D 1983 Toward tricyclo 2 2 2 2 decane 1 n 2 2 2 Paddlane systems n 10 14 Journal of the American Chemical Society 105 6 1656 doi 10 1021 ja00344a042 Hahn E H Bohm H Ginsburg D 1973 The synthesis of paddlanes Compounds in which quaternary bridgehead carbons are joined by four chains Tetrahedron Letters 14 7 507 doi 10 1016 S0040 4039 01 95684 9 See also editPropellane Fenestrane Inverted tetrahedral geometry nbsp This article about a hydrocarbon is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Paddlane amp oldid 1090194805, wikipedia, wiki, book, books, library,
