Allylation of Grignard reagents: its application for the synthesis of (4E, 7Z)-4,7-tridecadienyl acetate, a sex pheromone of potato tuberworm moth

Yadav, J. S. ; Satyanarayana Reddy, P. (1986) Allylation of Grignard reagents: its application for the synthesis of (4E, 7Z)-4,7-tridecadienyl acetate, a sex pheromone of potato tuberworm moth Synthetic Communications, 16 (9). pp. 1119-1131. ISSN 0039-7911

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Official URL: http://www.tandfonline.com/doi/abs/10.1080/0039791...

Related URL: http://dx.doi.org/10.1080/00397918608056355

Abstract

Alkylmagnesium halides have been found to react with (Z)-4-benzyloxy-1-chloro-2-butene in presence of HMPA to produce a rearranged product 3-alkyl-4-benzyloxy-1-butene, while in absence of HMPA a normal product (Z)-1-alkyl-4-benzyloxy-2-butene resulted as the predominant product. Latter product has been utilized for the synthesis of (4E, 7Z)-4,7-tridecadienyl acetate, a sex pheromone of potato tuberworm moth.

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