Tetrahedron

Experimental and theoretical investigations for the tandem alkylation–isomerization reactions between unsaturated carboxylic acids and allyl halides

LR Domingo, S Gil, M Parra, JA Sáez, M Torres

Index: Domingo, Luis R.; Gil, Salvador; Parra, Margarita; Saez, Jose A.; Torres, Mercedes Tetrahedron, 2003 , vol. 59, # 33 p. 6233 - 6239

Full Text: HTML

Citation Number: 11

Abstract

Alkylation of dienediolates from unsaturated carboxylic acids with allylic halides when followed by solventless thermal treatment at 150 to 200° C afford rearranged products on a trend highly dependent on the α carbon substitution. Thus, 2, 2-bisallylated acids with H atoms at C-2 lead to its 1, 3-shift, whereas 2-methyl-2, 2-bisallylated acids lead to the corresponding Cope rearrangement product. In the latter case, this tandem allylation- ...