by this reagent. Kishner-Wolff reduction of (+)-isopinocamphone (IIIa; R = =O) gave a poor yield of pinanes consisting of 87% (g.1.c.) of the trans-isomer.
Spectroscopic and oxidative studies of marrubiin, C2,,HZOO4, indicate that it is a furan derivative, having the structure (111).MARRUBIIN, a bitter principle of horehound (Marrubium vzdgare L), is extracted from the herb with acetone in yields of up to 1%, but different samples of the herb produce widely differing amounts, and some samples we examined yielded none. Season of harvesting, conditions of drying, and length of storage have a profound influence upon the yield, and it has been suggested (Rizzocath, Thesis, Univ. Aix-Marseille, 1933) that marrubiin is an artefact arising from an essential oil during the drying of the horehound. It is, of course, important that the herb should be of the correct botanical species. From time to time, BaZZota hirsuta Benthani has been sold as horehound; this contains little or no marrubiin, which can however be isolated in small yield from B. foetida (Balansard, Comfit. rend.
P-Cyano-a-methylcycloalkanones are regiospecifically nitrosated at the a-position by pentyl nitrite in methanolic sodium methoxide to give fused isoxazolo-lactams via a pathway probably involving sequential cycloalkanone cleavage, isoxazole formation and lactamisation. The chemistry of some new compounds derived from the hydrocyanation products of ( -)-carvone is described. I3C) were both consistent with the enol tautomer 24. The Me H 24 Paper 4/06628F
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