A synthetic approach to some bicyclo-[4,1,0]-heptane derivatives

Abstract

The bicyclo- [4, 1,0]-heptane system was first exemplified by Δ3 - carene (I), isolated from the essential oils of Pinus longifolia and originally mistaken for sylvestrene. Rabak, Pharm. Rev., 23, 229 (1905)., Schimmel's Report, p.66 (April, 1906), p.93 (October, 1911) Bull. Imp. Inst., 9, 8 (1911). Robinson suggested Robinson, Proc. Roy. Soc., 27, 247 (1911). that carene was a bicyclic terpene, which gave sylvestrene hydrochloride when treated with hydrogen chloride. The investigations of Simonsen and his collaborators showed Robinson's suggestion to be correct Simonsen et al., J. Chem. Soc., 117, 570 (1920); 123, 549 (1923); 133, 359 (1928); 135, 305 (1929)., and established the present accepted structure. d-Δ - carene occurs fairly frequently in nature Rao and Simonsen, J. Chem. Soc., 127, 2494 (1925). Semmler and Schiller, Berichte, 60, 1591 (1927). Aschan, Annalen, 461, 1 (1928). West, Perfumery Essential Oil Record, 29, 170 (1938). (A review). Mirov, J. Amer. Chem. Soc., 40, 410, 550 (1951); 43, 738 (1954); 44, 186 (1955); 45, 629 (1956). 1 -Δ3 -carene is also known Panicker, Rao and Simonsen, J. Ind. Inst. Sci., 9A, 137 (1926). Krestinski, Liverovski and Malmberg, J. Prakt. Chem., 129(ii), 97 (1931). Krestinski and Malevskaya, J. Appl. Chem. Russ., 12, 878 (1939). Duncan, Sherwood and Short, J. Soc. Chem. Ind. Trans., 50, 410 (1931). Ohloff-Fette and Seifen, Anstrichmittel, 56,605 (1954).