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37.1.3.9.2 Variation 2: Of Conjugated Alkenes

DOI: 10.1055/sos-SD-037-00085

Soenen, D. R.; Vanderwal, C. D.Science of Synthesis, (200837122.

Like alkyl-substituted cycloalkenes, the reactivity of phenylcycloalkenes toward photoalkoxylation depends on ring size. Irradiation of methanolic solutions of 1-phenylcycloalkenes 151 (Scheme 20) shows that alcohol addition to give ethers 152 only occurs to 1-phenylcyclohexene and 1-phenylcycloheptene, presumably by thermal addition of methanol to the trans-phenylcycloalkenes formed from the orthogonal excited states of 151 (n=2) and 151 (n=3). Formation of trans-phenylcyclopentene is presumably precluded by its inherent ring strain, and trans-phenylcyclooctene does not suffer enough strain to lower the energy barrier for methanol addition.[‌94‌]

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