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Actuating Cycloaromatization of a Bicyclo[7.3.1]enediyne by Annelation: An Example of Inverse Dependence on Bridge Atom Hybridization
Journal article   Peer reviewed

Actuating Cycloaromatization of a Bicyclo[7.3.1]enediyne by Annelation: An Example of Inverse Dependence on Bridge Atom Hybridization

Michael H Nantz, David K Moss, John D Spence and Marilyn M Olmstead
Angewandte Chemie (International ed.), Vol.37(4), pp.470-473
03/02/1998
DOI: https://doi.org/10.1002/(SICI)1521-3773(19980302)37:4<470::AID-ANIE470>3.0.CO;2-Q
Handle:
https://hdl.handle.net/20.500.12741/rep:9118
PMID: 29711152

Abstract

Enediynes Kinetics Annulation Spiro compounds Cycloaromatizations
Although the acetylenic carbon atoms in 2 are closer together than those in 1, only the latter undergoes Bergman cyclization. In contrast, in analogous enediynes without an annelated cyclohexane ring a change in the hybridization of the bridging carbon atom from sp to sp leads to a dramatic increase in the cyclization rate.

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