ISSN:
1573-9171
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Conclusions 1. A study has been made of the reaction of 1,2-dimethyldecahydroquinolones, isomeric at C-2, ethynyl-, vinyl-, and ethylmagnesium bromides. 2. The reaction of 1,2-dimethyldecahydro-4-quinolone (I), possessing an equatorial methyl group at C-2, with ethynylmagnesium bromide yielded a mixture of two possible epimers of 1,2-dimethyl-4-ethyldecahydro-4-quinolol with a marked predominance in the mixture, of acetylenic alcohol with axially arranged ethynyl group at C-4. 3. An opposite stereochemistry of addition was observed in the reaction of 1, 2-dimethyldecahydro-4-quinolone (I) with vinylmagnesium bromide or ethylmagnesium bromide. The product was a mixture of two epimers of 1,2-dimethyl-4-vinyldecahydro-4-quinolols or 1,2-dimethyl-4-ethyldecahydro-4-quinolols in which the main isomer present was the one having the vinyl or ethyl group arranged equatorially. 4. 1,2-Dimethyldecahydro-4-quinolone (II) possessing axial methyl group at C-2 in each of the three cited reactions owing to the strong 1,3-interaction yielded only one alcohol epimer 1,2-dimethyl-4-ethynyl(4-vinyl, 4-ethyl) decahydro-4-quinolol in which ethynyl, vinyl, and ethyl substituents at C-4 are arranged equatorially.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00861490
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