Formation of an Isomeric Mixture of Dienynes Instead of a Diallene

Abstract

Attempts to convert 1,1,2,2,7,7,8,8-octaethoxyocta-3,5-diyne to a symmetric allene by reduction with lithium aluminum hydride failed. Instead reduction accompanied by isomerization occurred and afforded 1,1,2,7,8,8-hexaethoxyocta-2,6-dien-4-yne as a mixture of three isomers in 63% total isolated yield.

Editorial: Special Issue “Molecules from Side Reactions”

“…During their study to prepare an intermediate to be attached to a solid support, they found an interesting side product with a seven-membered ring [11]. In the eleventh paper, the formation of an isomeric mixture of dienynes, instead of a diallene, was detected during a reduction reaction performed on the 1,1,2,2,7,7,8,8-octaethoxyocta-3,5-diyne [12]. In the twelfth paper, the authors reported on the synthesis of a new pyrrole-substituted terpyridine derivative that possessed an allene moiety.…”