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1,2 and 1,4 addition of group IVA anions to 2-cyclohexenones. Kinetic and thermodynamic product control.

โœ Scribed by W. Clark Still; Abhijit Mitra


Publisher
Elsevier Science
Year
1978
Tongue
French
Weight
237 KB
Volume
19
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


For many years there has been a lively controversey on the mechanism of nucleophilic 1,2 and 1,4 additions to a,@-unsaturated carbonyl compounds.

Various arguments based on reversibility, electron transfer, geometry and hard soft acid base (HSAB) theory have been advanced to explain experimental obser-


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afforded Diels-Alder adduct 14 and fragmentation product 32 with 2 and 3 respectively whereby reaction occurred on the less substituted double bond. No adducts were isolated upon treatment of naphthoquinone-sulfide 22 with either 2 or 3. The Diels-Alder adducts of benzoquinone-sulfoxide 9 and naphth