By K H Overton
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114)], known to occur on gas ~ h r o m a t o g r a p h y , was ' ~ ~ not taken into account. '59 ' Nitration of p-cymene (117; R' = R 2 = H) has been known for well over a century to yield p-nitrotoluene by ips0 electrophilic attack (nitrodeisopropylation); now a novel mechanism, based on the idea of the C-1 position as that most active towards attack by nitronium ion, is supported by the isolation of up to 41 % of the ipso-adducts (1 18 ; cis and trans) and 41% of 2-nitrocymene (117; R' = H, R2 = NO,).
N. Bosworth and P. D. S. Perkin I, 1973, 2319. ~~~ The radical-initiated photoaddition of N-nitrosopiperidine to a-pinene, in contrast, leads to menthanes only above 0 "C(Scheme 19). Below - 40 "C,addition of the nitroxide radical to the initially formed 289 290 291 292 293 294 295 296 29' A. Yoshikoshi, Y . Takagi, and T. Akiyama, Jap. , 91 04611973, 91 04711973. G. Feuillerat and J. Sotiropoulos, Compt. , 1974, 279, C, 71. T. D. R. Manning, Tetrahedron Letters, 1974, 2669. T. Gibson, J . Org.
Agosta, J . C . S . Chem. , 1973,771. M. T. Thomas and A. G. Fallis, Tetrahedron Letters, 1973, 4687. 38 Terpenoids and Steroids X = NH,) are consistent with a ‘hot’ ion (205)273,274 and somewhat different from those arising from carbonium ions produced by the action of potassium hydroxide on pinanols. The unexpected production of the pinan-2-01 (206) in 28% yield from cismyrtanol (204; X = OH) and potassium hydroxide is explained by the capture of a hydroxide ion by the carbonium ion (207; R’ = R’ = H) so fast that the initial cis stereochemistry is retained.