The photo-cycloaddition of enol ethers to benzene

Andrew Gilbert, Grahame N. Taylor, Mohd Wahid Bin Samsudin

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

The photo-reactions of benzene with ethyl vinyl ether, n-butyl vinyl ether, 1,1-dimethoxyethylene, 2,3-dihydropyran, 2,3-dihydrofuran, 2,3-dihydro-1,4- dioxin, and 1,3-dioxole are described. The meta-photo-cycloaddition of ethyl vinyl ether and n-butyl vinyl ether to benzene shows little selectivity, and regio- and stereo-isomers are isolated. ortho-Cycloaddition is observed from all systems but only with 2,3-dihydrofuran as addend are both stereoisomers of the adduct formed, and although the exo-isomer is very photolabile, the endo-product is essentially stable under its conditions of formation. The ortho-cycloaddition of 1,1-dimethoxyethylene to benzene provides the first step in a convenient synthesis of cyclo-octatrienone. Contrary to previous proposals there is little correlation between the stereochemistry of the ortho-cycloaddition and preferred orientation of the addends in the ground state. The relationship between the relative efficiency of the two addition modes and ionisation potential of the ethylene is discussed.

Original languageEnglish
Pages (from-to)869-876
Number of pages8
JournalJournal of the Chemical Society, Perkin Transactions 1
Publication statusPublished - 1980
Externally publishedYes

Fingerprint

Ethers
Cycloaddition
Benzene
Isomers
Stereochemistry
Stereoisomerism
Ionization potential
Crystal orientation
Ground state
2,3-dihydrofuran
ethyl vinyl ether
n-butyl vinyl ether

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Gilbert, A., Taylor, G. N., & Bin Samsudin, M. W. (1980). The photo-cycloaddition of enol ethers to benzene. Journal of the Chemical Society, Perkin Transactions 1, 869-876.

The photo-cycloaddition of enol ethers to benzene. / Gilbert, Andrew; Taylor, Grahame N.; Bin Samsudin, Mohd Wahid.

In: Journal of the Chemical Society, Perkin Transactions 1, 1980, p. 869-876.

Research output: Contribution to journalArticle

Gilbert, Andrew ; Taylor, Grahame N. ; Bin Samsudin, Mohd Wahid. / The photo-cycloaddition of enol ethers to benzene. In: Journal of the Chemical Society, Perkin Transactions 1. 1980 ; pp. 869-876.
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