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

Article Article scientifique Article Stereospecific, R2AlCl-Promoted Intramolecular Ene Reaction of a 1,6-Dienoate: Evidence for a Concerted Mechanism eng 1984-05-02 author Von Oppolzer Wolfgang 25270 author Mirza Sohail Mahmood 74075 730-738 10.1002/hlca.19840670312 0018-019X https://onlinelibrary.wiley.com/doi/10.1002/hlca.19840670312 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). Dewey 540 36 Département de chimie organique 141 false Helvetica chimica acta 67 3 a4ff4018-6726-4917-bc95-acf1769a9655 Article (Published version) Restricted Oppolzer_HCA_198467730.pdf 506207 application/pdf 574821dfe822a4835d5dc7422698ad2b34f9933a3cb0ebbc9c315ce6a453002e restrictedAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Title	Published in	Access level	OA Policy	Year	Views	Downloads

Stereospecific, R₂AlCl-Promoted Intramolecular Ene Reaction of a 1,6-Dienoate: Evidence for a Concerted Mechanism	Helvetica chimica acta			1984	78	0

Archive ouverte UNIGE

Mirza, Sohail Mahmood