I. N. Nazarov, L. V. Torgov, I. I. Zaretskaya
1953
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Journal
Russian Chemical Bulletin
Abstract
1. A. detailed investigation has been made of the conditions for the condensation of 2-methyl-2-cyclohexen-1-one (II) with 2-methoxy-1,3-butadiene (I). 2. It has been shown that this condensation proceeds in two directions with formation of 2,3,4a,5,8,8a-bexahydro-6-methoxy-8a-methyl-1(2H)-naphthalenone (III), and 2,3,4a,5,8,8a-hexahydro-7-methoxy-8a-methyl-1(2H)-naphthalenone (IIIa) in a ratio of approximately 5:1. The yield of condensation products has been increased from 25 to 45–50%. 3. A detailed study has been made of the condensation of the compounds III and IIIa with alkali-metal acetylides in liquid ammonia. By this means yields of 50–55% of the acetylenic hydroxy ketones (V) and (Va) have been obtained, and these have been hydrogenated selectively in the presence of a Pd catalyst, yielding the vilyl hydroxy ketones (VI) and (VIa), which have been dehydrated with potassium hydrogen sulfate to give the d?enomes (VII) and (VIIa). The structures of these dienones and related compounds have been rigorously proved by converting them into known methylchrysenes (XX and XXa), and also by converting the dienone (VII) into the known 2-methylphenanthrene.