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1983•Journal of the Chemical Society Perkin Transactions 1Requires access

trans-Cycloalkenes. Part 12. trans,trans- and cis,trans-Cyclonona-1,5-diene

A. Christopher Connell, Gordon H. Whitham

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Abstract

Possible synthetic routes to trans,trans-cyclonona-1,5-diene from the cis,cis-isomer have been investigated using the β-hydroxyphosphine oxide olefin inversion procedure. A stepwise approach via the epoxy-trans-cyclononene (10) failed. However consecutive double elimination involving the bis-β-hydroxyphosphine oxides (11) and (12) gave cis- and trans-1,2-divinylcyclopentane which are believed to have been obtained by rapid Cope rearrangement of first formed ‘parallel’ and ‘crossed’trans,trans-cyclonona-1,5-diene (1A) and (1B) respectively.

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What this paper is about

Possible synthetic routes to trans,trans-cyclonona-1,5-diene from the cis,cis-isomer have been investigated using the β-hydroxyphosphine oxide olefin inversion procedure. A stepwise approach via the epoxy-trans-cyclononene (10) failed. However consecutive double elimination involving the bis-β-hydroxyphosphine oxides (11) and (12) gave cis- and trans-1,2-divinylcyclopentane which are believed to have been obtained by rapid Cope rearrangement of first formed ‘parallel’ and ‘crossed’trans,trans-cyclonona-1,5-diene (1A) and (1B) respectively.

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Available abstract

Possible synthetic routes to trans,trans-cyclonona-1,5-diene from the cis,cis-isomer have been investigated using the β-hydroxyphosphine oxide olefin inversion procedure. A stepwise approach via the epoxy-trans-cyclononene (10) failed. However consecutive double elimination involving the bis-β-hydroxyphosphine oxides (11) and (12) gave cis- and trans-1,2-divinylcyclopentane which are believed to have been obtained by rapid Cope rearrangement of first formed ‘parallel’ and ‘crossed’trans,trans-cyclonona-1,5-diene (1A) and (1B) respectively.

Key concepts: Diene, Cis–trans isomerism, Chemistry, Stereochemistry, Olefin fiber, Medicinal chemistry, Organic chemistry, Catalysis

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