Reactions of 3,7-Dimethyloctadienes and their Derivatives

Reactions of 3,7-Dimethyloctadienes and their Derivatives.—Geraniol and nerol were sequentially converted into their chlorides and cyanides with no allylic rearrangement on treatment with (Bun)3P-CCl4-KCN in the presence of crown ether.175 2,4,6-Trichloro-4-bromocyclohexa-2,5-dienone selectively brominated geraniol derivatives (functionalized at C-l) under mild conditions to give the 

Mandai, H. Yamaguchi, K. Nishikawa, M. Kawada and J. Otera, Tetrahedron Lett., 1981, 22, 763. 

Kleijn, H. Westmijze, J. Meijer, and P. Vermeer, Reel. Trav. Chim. Pays-Bas, 1980, 99, 340. 178 Y. Ueno, H. Sano, S. Aoki, and M. Okawara, Tetrahedron Lett., 1981, 22, 2675. 

7-dibromo-compounds together with products substituted at C-10 and at C-6.176 10-Bromogeranyl methyl ether was readily isomerized to the 8-bromo-compound and products of allylic rearrangement.177 The isomers of 2,3-epoxygeraniol yielded 1,2-dihydroxy-myrcene and -ocimene on treatment with Ti(OPr )4 however, 

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