E/Z isomerism without a double bond - An unusual type of stereoisomerism, and an unprecedented isomerisation in a bicyclobutane

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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.

Translated title of the contributionE/Z Isomerie ohne Doppelbindung: - ein ungewöhnlicher Typ von Stereoisomerie, und eine beispiellose Isomerisierung in einem Bicyclobutan.
Original languageEnglish
JournalCroatica Chemica Acta
Volume77
Issue number1-2
Pages (from-to)237-241
Number of pages5
ISSN0011-1643
Publication statusPublished - 05.2004
Externally publishedYes

    Research areas

  • Chemistry
  • E/Z isomerism, Isomerisation, Rearrangement, Stereoisomerism, Substituted bicyclo[1.1.0]but-1(3)-ene, Substituted bicyclobutanes, Thia[1.1.1]propellane

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