Abstract
1. The condensation of isoprene with 2-methyl-2-cyclohexen-1-one (I) was studied, and it was shown that the main product of this reaction is the para isomer, cis-3,4,4a,5,8,8a-hexahydro-6,8a-dimethyl-1(2H)-naphthalenone (II), the structure of which was proved by its conversion into 1,6-dimethylnaphthalene (VII). 2. Condensation of the hexahydro-1(2H)-naphthalenone (II) with sodium acetylide in liquid ammonia gave a 90% yield of the acetylene alcohol (IX), which was converted by selective hydrogenation into the ethylenic alcohol (XI). Dehydration of (XI) gave 1,2,4a,5,8,8a-hexahydro-4a, 7-dimethyl-4-vinylnaphthalene (XII) in an overall yield, taken over all stages, of more than 50%. 3. The cis triene (XII) was condensed with maleic anhydride and with dimethyl fumarate, and mixtures of stereoisomeric adducts, (XIII) and (XIV), were obtained in high yield.
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