Original scientific paper

π-Facial Selectivity in Diels-Alder Cycloadditions

Alan P. Marchand ; Department of Chemistry, University of North Texas, Denton, Texas 76203-5070, USA
Hyun-Soon Chong ; Department of Chemistry, University of North Texas, Denton, Texas 76203-5070, USA
Bishwajit Ganguly ; Department of Chemistry, University of North Texas, Denton, Texas 76203-5070, USA
James M. Coxon ; Department of Chemistry, University of Canterbury, Christchurch, New Zealand

Abstract

Diels-Alder reactions between π-facially differentiated dienes and/or π-facially differentiated dienophiles frequently proceed with remark-able π-facial selectivity. Experimental and theoretical studies have been undertaken in an effort to gain insight into the fundamental origins of this phenomenon. Reactions of interest in this connection include thermal [4 + 2] cycloadditions between (i) various dienophiles and cage-annulated 1,3-cyclohexadienes (i.e. systems 1, 4, 6, and 9) and (ii) various dienes and cage-annulated dienophiles (i.e. systems 1a, 11a, and 14). The results of relevant molecular mechanics, semiempirical, and ab initio molecular orbital calculations generally are consistent with experiment.

Keywords

π -facial selectivity; Diels-Alder cycloadditions

Hrčak ID:

131985

URI

https://hrcak.srce.hr/131985

Publication date:

4.12.2000.

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