Halogenated terpenoids. IX. Further terpinolene tetrahalide derivatives

The syntheses of new 1,2,4,8-, 1,2,8,9-, and 1,4,7,8-tetrahalides of p- menthane are described in both optically active and racemic series. Vicinal dihalo rearrangements in the optically active terpinolene (1,2,4,8-) series provide proof of the involvement of the C4, C8 bromines during the rearrangement of terpinolene tetrabromide.