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A Review of the literature published between September 1970 by K H Overton

By K H Overton

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R . Ryan, Tetrahedron Letters, 1971, 129. Z . Chabudzinski, U . Lipnicka, and Z . , 1970, 44, 2181 A. Coulombeau and A . Rassat, Bull. Soc. chim. France, 1970, 4389. W. Hiickel and H. , 1971,44, B, 61. Terpenoids and Steroids 44 (239) (240) 3-toluene-p-sulphonate (241)leads to the exo-epoxide (242),and similar treatment of the endo,endo-dihydroxy-compound leads to the endo-epoxide (243). Acid treatment of the epoxide leads, in the case of the endo-epoxide, to the bicyclic ketone (244), but the exo-epoxide (242) gives a ring-opened aldehyde (245).

McDaniel, J . Soc. Cosmetic Chemists, 1971, 22, 15. 9 9 J . D. McChesney and A . F. Wycpalek, Chem. , 1971, 542. l o o P. Singh, Tetrahedron Letters, 1970, 4089. *Further aspects of odour and optical activity of monoterpenoids are discussed by Theimer and M ~ D a n i e l . ~ ~ 94 Monoterpenoids 27 0 Li-MeI-NH, ____+ A (133a) p"0 (135) (133b) + /I\' H (136) (137a) H (137b) The optical rotations of the N-acetyl-N-alkyl-menthylamines and the four 3-methoxymenthanes in different solvents have been studied by Voisin and Gastambide,"' who discuss the conformational equilibria.

1, p. -Two full papers have appeared on subjects mentioned in Vol. 1 : Demole and Enggist's karahanaenone synthesis,' 40 and the irradiation of eucarvone. 141 Another paper concerning the irradiation of eucarvone has appeared ; in this case the substrate was protonated by carrying out the reaction in fluorosulphonic acid at - 78 "C. The products obtained after quenching the reaction with potassium carbonate in methanol are shown in Scheme 5, together 13' 13' 139 140 14' R. N . Gedye, A . C . Parkash, and K.

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