Pinocarveol

Pinocarveol, CjjHjgO, is a bicycUc alcohol, which has heen found irr oil of Eucalyptus globulus, and is apparentlyddentical with the alcohol obtained by the reduction of nitrosopinene. It can be prepared artificially in the following manner —... [Pg.138]

Seventy grams of pinylamine nitrate are treated with a solution of 10 grams of sodium nitrite in 100 c.c. of water for some time. The yellowish oil which separates is distilled with steam, and the distillate is shaken with an oxalic acid solution in order to remove basic compounds, and again distilled with steam. Pinocarveol has the following characters —... [Pg.138]

It forms a phenylurethane which appears to consist of two isomers melting at 82° to 84° and at 94° to 95° respectively. The formation of these two phenylurethanes makes it probable that pinocarveol is itself a mixture of two isomeric compounds. On oxidation with chromic acid pinocarveol yields a compound CjqHj40 which forms two semi-carbazones,. melting at 210° and 320° respectively. [Pg.138]

ALLYLIC OXIDATION WITH HYDROGEN PEROXIDE-SELENIUM DIOXIDE frans-PINOCARVEOL... [Pg.25]

BASE-INDUCED REARRANGEMENT OF EPOXIDES TO ALLYLIC ALCOHOLS trans-Pinocarveol,... [Pg.55]

Pinen—3a-ol, 53, 17 fcrans-Pinocarveol, 53, 17 Pivalaldehyde, by condensation of tert-butylmagnesium bromide with 1,1,3, 3-tetra-methylbutyl isonitrile, 51, 38... [Pg.134]

Isopinocampheol has been prepared by hydrogenation of irams-pinocarveol with a neutral nickel catalyst at 70-100°. The hydroboration reaction provides a convenient procedure for the conversion of olefins to alcohols without rearrangement and with a predictable stereochemistry. The reaction has been applied to a large number of olefins of widely different structures. The results obtained support the proposed generaliza-tit)ii that hydroboration involves an anborane from the less hindered side of the double bond. ... [Pg.111]

The same authors also reported the dehydrogenation of pinocarveol to pino-carvone and pinocampheol to pinocamphone catalyzed by MgO (197) (Scheme 37). Pinocampheol was oxidized to the corresponding ketone with yields in the range of 40%, whereas the yields of pinocarvone from pinocarvenol did not exceed 10%. [Pg.274]

Oxidative cleavage of monocyclic and bicyclic allylic alcohols to keto acids and di-acids respectively is effected by RuClj/aq. Na(IO )/CCl -CH3CN thus trans-verbenol gave (+)-c/x-pinononic acid and (+)-frani-pinocarveol yielded (-)-cis-pinic acid (Table 3.6) [237]. The double bond in diphenylcholene was cleaved by RuOj/aq. Na(IO )/CCl to aldehyde and acid (Table 3.4) and the adjoining phenyl rings destroyed [238]. [Pg.200]

Bicyclo[3,l,l]heptanes.—Spin-lattice relaxation time measurements have facilitated the n.m.r. spectral assignments of paeoniflorin and albiflorin (Vol. 3, p. 71). trans-Pinocarveol (223) has been synthesized from /3-pinene in t-butyl alcohol with hydrogen peroxide in the presence of a catalytic amount of selenium... [Pg.53]

R-Me) with none of the well known ring-contracted ketone which is observed in protic solvents (Vol. 2, p. 54 Vol. 4, p. 63 Vol. 5, p. 41). Similar reaction of the isomeric 2a-hydroxy-3/3-tosyloxypinane yields trans-pinocarveol (223 74%) presumably via 2a,3a-epoxypinane (Vol. 6, p. 44). °... [Pg.55]

Cinnamomum camphora (L.) J. S. Presl. Chang Shu (Cinnamon) (root, branch, leaf) d-camphor, eucalyptole, cineole, pinene, aromadendrene, cumaldehyde, pinocarveol, l-acetyl-4- isopropy lidenecy clopentene33 -53 Stimulate nervous system, relax gastrointestinal muscle contractions. [Pg.53]

BASE-INDUCED REARRANGEMENT OF EPOXIDES T 0 ALLYLIC ALCOHOLS trans- PINOCARVEOL... [Pg.17]

Pinocarveol has been prepared by the autoxidation of a-pinene,5 by the oxidation of /S-pinene with lead tetraacetate,6 and by isomerization of a-pinene oxide with diisobutylalumi-num,7 lithium aluminum hydride,8 activated alumina,9 potassium ferf-butoxide in dimethylsulfoxide,10 and lithium diethylamide.11 The present method is preferred for the preparation of pinocarveol, since the others give mixtures of products. It also illustrates a general method for converting 1-methylcy-cloalkene oxides into the corresponding exocyclic methylene alcohols.11 The reaction is easy to perform, and the yields are generally high. [Pg.20]

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