Stereospecific, R<sub>2</sub>AlCl-Promoted Intramolecular Ene Reaction of a 1,6-Dienoate: Evidence for a Concerted Mechanism

Von Oppolzer, Wolfgang; Mirza, Sohail Mahmood

doi:10.1002/hlca.19840670312

Scientific article

English

Stereospecific, R₂AlCl-Promoted Intramolecular Ene Reaction of a 1,6-Dienoate: Evidence for a Concerted Mechanism

ContributorsVon Oppolzer, Wolfgang; Mirza, Sohail Mahmood

Published inHelvetica chimica acta, vol. 67, no. 3, p. 730-738

Publication date1984-05-02

Abstract

Treatment of the 83%-trans-¹³CH₃-labelled 1,6-dienoate 7 with Et₂AlCl at–78° provided in high yield the ene product 9 containing 83% ¹³C localized in the olefinic C(8)-methylene group. Accordingly, H-transfer occurs exclusively from the trans-methyl group of 7, consistent with a concerted ene process 7 9 thereby ruling out an intermediate cation 8 (Scheme 4).

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

VON OPPOLZER, Wolfgang, MIRZA, Sohail Mahmood. Stereospecific, R₂AlCl-Promoted Intramolecular Ene Reaction of a 1,6-Dienoate: Evidence for a Concerted Mechanism. In: Helvetica chimica acta, 1984, vol. 67, n° 3, p. 730–738. doi: 10.1002/hlca.19840670312

Article (Published version)

Identifiers

PID : unige:168009
DOI : 10.1002/hlca.19840670312

Additional URL for this publicationhttps://onlinelibrary.wiley.com/doi/10.1002/hlca.19840670312

Journal ISSN0018-019X

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Stereospecific, R2AlCl-Promoted Intramolecular Ene Reaction of a 1,6-Dienoate: Evidence for a Concerted Mechanism

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Stereospecific, R₂AlCl-Promoted Intramolecular Ene Reaction of a 1,6-Dienoate: Evidence for a Concerted Mechanism