By K H Overton
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Additional info for A Review of the literature published between September 1974 and August 1975
10 422 incorrectly names (170; R1= Me, R2 = Ph)]. * Chemical Abstracts does not use the prefix 'iso' used in these Reports. Terpenoids and Steroids 36 (170) (170; R'= Me or Ph, R2= Ph) have the two dipoles, C=O and C=S, unfavourably aligned by steric constraints. d. r. r. r. Vol. 5, p. Vol. 3, p. 59 for related work). The previously reported (Vol. 4, p. 44; cf. Vol. 5 , p. 3 1) lower stereospecificity reported by Stothers for the racemization of camphene with acid may be interpreted as involving less internal stabilization of (171) via C-2-C-6 bonding in the presence of the more nucleophilic solvent used.
Filippova, N. I. Zakharova, and C. I. Sarnokhvalov,J. Org. Chem. ),1974, 10,1873. T. Kishimoto and Y. Matsubara, Nippon Nagaku Kaishi, 1975, 701. B. Corbier and P. Teisseire, Recherches, lY74, 19, 253. H. R. Ansari and R. Clark, Tetrahedron Letters, 1975, 3085. 19 Monoterpenoids Reagents: i, HNO,; ii, LiAlH,; iii, p-TsCl-py; iv, aq. KOH; v, diethyl malonate-NaOEt; vi, aq. KOH; vii, aq. H,SO,; viii, CH,O-Et,NH; ix, PhSeH; x, BulAlH-THF; xi, Ph,P( Me)Br-NaH-DMSO. -A separate section is devoted this year to halogenated monoterpenoids: twenty-four acyclic and four cyclic compounds in this class have been reported.
Yarnada, Chem. and Pharm. Bull. (Japan), 1975, 23. 279. *4h R. S. Becker, S. Berger, D . K. Dalling, D. M . Grant, and R. J. Pugmire, J. Amer. Chem. ,1974,96, 7008. 247 L. E. Brady, D. H. Williams, S. C. Traynor, and K . J . Crowley. Org. Mass Spectrometry, 1975,10, 1 16. 24x W. Cocker, K. J . Crowley, and S. G . S. Chen. , 1974,982. *4v S. Torii. K. Uneyama, and M. Isihara, Chem. Letters, 1975, 479. -Two new halogenated monoterpenoids are violacene (150) from Plocarniurn v i o l a c e ~ r na, ~1,4-dimethyl~~ 1-ethylcyclohexane which can be rationalized biosynthetically from the cyclization of an acyclic precursor via a bromonium ion, and plocamene B (15 l), again from Plocarniurn violaceurn, which may be the first member of a series of non-isoprenoid monoterpenoids from this species .
A Review of the literature published between September 1974 and August 1975 by K H Overton