Raymond M. Carman

The isomeric 1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octan-6-ol (2-Hydroxy-1,8-cineoles)

The stereochemistry of the title compounds, and of the two 1,2-epoxy-p-menthan-8-ols, is discussed.

The reaction of tertiary alcohols with phosphorus pentachloride

Reaction with phosphorus pentachloride under extremely mild conditions is a method of choice for the synthesis of tertiary chlorides from tertiary alcohols with retention of configuration.

Halogenated terpenoids. XX: The seven monochlorocineoles

The seven monochlorocineoles have been synthesized, separated and characterized. Initial attempts to identify these compounds as pollutants in chlorinated water supplies from eucalypt-vegetated areas are discussed.

Antifungal diene in leaves of various avocado cultivars

Leaves (both young and mature) of seventeen commercial avocado (Persea americana) cultivars have been analysed monthly throughout the year to measure the concentration and seasonal variation of the antifungal diene (Z,Z)-2-hydroxy-4-oxohenicosa-12,15-dien-1-yl acetate (persin)

Some simple cyanoformaldehyde phenylhydrazones

The triazole ring of 2-phenyl-1,2,3-triazole-4-carboxylic acid is cleaved by alkaline treatment. The synthesis and stereochemistry of some simple cyano-formaldehyde phenylhydrazones is discussed.

The 3-Hydroxycineoles

Data concerning the 3-hydroxycineoles 1 and 2 are provided to enable the ready identification of these metabolites and to determine their enantiomeric excess in mixtures. An unusual S(N)2-type inversion at a tertiary center is observed during one synthetic approach.

Amino oximes from p-Menth-1-ene, Limonene and α-Pinene

Substituted α-amino oximes in the menthane and pinane series show interesting configurational and conformational effects. A further example of a boat conformer is described.

9,10-Dihydroxy-1,8-cineole (1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane-10,11-diol)

The title compound (3) has been synthesized and its presence sought in the urinary metabolites of the brushtail possum.

The isolation of (R)-2-Hydroxy-4-oxohenicosan-1-yl acetate from avocado leaves

(R)-2-Hydroxy-4-oxohenicosan-1-yl acetate (1b) can be readily isolated from avocado leaves after hydrogenation of the crude dichloromethane extract.

Sylvestrene nitrosochloride and derived amino oximes

Configurational and conformational effects in amino oximes derived from sylvestrene (m-mentha-6, 8-diene) nitrosochloride are discussed in terms of o.r.d. and H n.m.r. observations.