Original scientific paper

E/Z Isomerism Without a Double Bond – an Unusual Type of Stereoisomerism, and an Unprecedented Isomerisation in a Bicyclobutane

Christoph Rücker orcid.org/0000-0002-9287-3153 ; Institut für Organische Chemie und Biochemie, Universität Freiburg, D-79104 Freiburg, Germany
Gunter Haftstein ; Institut für Organische Chemie und Biochemie, Universität Freiburg, D-79104 Freiburg, Germany

Abstract

An unusual kind of stereoisomerism termed E/Z isomerism without a double bond or generalised E/Z isomerism is discussed for the first time. Examples are given of pairs of synthesized and separated compounds related by this kind of isomerism (4a/5a and 12a/15a), which were obtained by an unusual rearrangement of substituents on a bicyclobutane ring system. Conditions for the occurrence of generalised E/Z isomerism are defined.

Keywords

E/Z isomerism; stereoisomerism; substituted bicyclobutanes; isomerisation; rearrangement; substituted bicyclo[1.1.0]but-1(3)-ene; thia[1.1.1]propellane

Hrčak ID:

102668

URI

https://hrcak.srce.hr/102668

Publication date:

31.5.2004.

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