The [4.4.4.4]Fenestranes and[2.2.2.2]paddlane. Prospects for the realization of planar tetracoordinate carbon?

Würthwein, Ernst-Ulrich ; Chandrasekhar, Jayaraman ; Jenmis, Eluvathingal D. ; Schleyer, Paul von Rague (1981) The [4.4.4.4]Fenestranes and[2.2.2.2]paddlane. Prospects for the realization of planar tetracoordinate carbon? Tetrahedron Letters, 22 (9). pp. 843-846. ISSN 0040-4039

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/004040...

Related URL: http://dx.doi.org/10.1016/0040-4039(81)80011-1

Abstract

Semi-empirical (MINDO/3 and UNDO) MO calculations on highly strained planar tetracoordinate carbon candidates indicate the central carbons in cis [4.4.4.4] fenestrane (1̲) to have pyramidal (1a̲) and in trans-[4.4.4.]fenestrane (2̲) to have distorted tetrahedral (2a̲) geometries. In [2.2.2.2]paddlane (3̲), the two central carbons are pentacoordinate. Each is nearly coplanar with four carbon neighbours; additionally, the two bridgehead carbons are connected by a single bond (3a̲).

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