Preparation of 2-Alkenylsilanes and 2-Alkenylstannanes by the Reaction of 2-Alkenyl-1,1-cyclopropanedicarboxylate Esters with PhMe2SiAlEt2 and (Ph3Sn)2Zn. Generation of 2-Alkenyl-3-cyclopentene-1,1-dicarboxylates via Alkenyl-Substituted ?-Allylpalladium Complexes Derived from ...

DOI: 10.1246/bcsj.60.2509

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Bulletin of the Chemical Society of Japan p. 2509 - 2516 (1987)

Update date:2022-08-04

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Authors:

Fugami, Keigo

Oshima, Koichiro

Utimoto, Kiitiro

Nozaki, Hitosi

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Article abstract of DOI:10.1246/bcsj.60.2509

Reaction of 2-vinyl-1,1-cyclopropanedicarboxylate with PhMe2SiAlEt2, PhMe2SiZnEt2Li, or (Ph3Sn)2Zn gave 1,7-homoconjugate addition products, 2-alkenylsilanes or 2-alkenylstannanes.In a similar fashion, 2-(1,3-butadienyl)-1,1-cyclopropanedicarboxylate provided the corresponding 1,9-homoconjugate adducts, dienylsilanes or dienylstannanes.The adducts were converted into ?-allylpalladium complexes by means of .Treatment of the alkenyl-substituted ?-allylpalladium complexes derived from dienylsilanes and with bases such as PPh3 or Na2CO3 gave 2-alkenyl-3-cyclopentene-1,1-dicarboxylates.In contrast, the reaction of the ?-allylpalladiums generated from 2-alkenylsilanes and with the bases resulted in the formation of original vinylcyclopropane derivatives.

Full text of DOI:10.1246/bcsj.60.2509

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