Using data from the Walnut Creek Contraceptive Drug Study (a prospective study begun in 1969 and continuing to the present), Minnesota Multiphasic Personality Inventory-(MMPI) measured scores for depression of 8932 women were studied in relation to the incidence of breast cancer. No statistically significant association between MMPI scores for depression and the subsequent development of breast cancer was found. There was neither an association of risk of breast cancer with repression/sensitization as measured on the MMPI nor with scores on the MMPI lie scale. This study is unique because it represents the largest reported prospective cohort in which the association between depression and breast cancer development has been examined.

Friedel-Crafts cyclization of the acid chloride from optically active cisor tra«s-2-phenylcyclopropanecarboxylic acid (cis-and trans-) gave racemic l,la,6,6a-tetrahydrocycloprop[a]inden-6-one (3). Uncyclized acid (from pure cisor trans-) was completely racemized, and was 15% cis-1 and 85% trans-1; optically active 3 did not racemize under Friedel-Crafts conditions. Cyclopropane ring opening and complete equilibration occur among epimeric and enantiomeric species before acylation takes place; involvement of homoketenyl cations is proposed, and precedents are cited. Acid chloride from active cis-1 with thionyl chloride in refluxing benzene gave no intramolecular acylation. There was also no effect on the activity of recovered starting material, but epimerized (trans) product was partly racemized; configurational inversion occurred predominantly at the asymmetric center bearing the acid chloride function. No evidence was obtained requiring that two-center inversions of cyclopropyl compounds be concerted. Reversiblesolvolytic ring opening of substituted l cyclopropanes has received much attention recently; evidence has been advanced for the interconvertibility of -cyclopropylvinyl and homoallenyl cations,2 and for racemization of suitably substituted cyclopropanes via ionic intermediates.3 This paper reports evidence for what is believed to be the first example of racemizing interconversion of cyclopropacyl and homoketenyl cations.Indications of this phenomenon were uncovered during attempts to establish the absolute configuration of 1,1 a,6,6a-tetrahydrocycloprop[a]indene (1) through correlation with cisor lram-2-phenylcyclopropanecarboxylic acid (cis-and trans-1), configurations of which are known.4 The intramolecular Friedel-Crafts acylation reaction of acid chloride from racemic transit was modified to give ketone 3 in over 70% yield.3 However, when acid chloride from (-)-trans-l, [ ]26 -309°( c 1.5, 95% ethanol), was subjected to the same Friedel-Crafts conditions, the ketone (3) obtained was racemic, as was all recovered uncyclized acidic material. The latter consisted of 15% cis-2 and 85% trans-2. Hydrolysis of a sample of the same acid chloride which had not been exposed to Lewis acid afforded (-)-trans-l having essentially unchanged optical activity.Optically active 3, obtained by selective Schiff base(1) Part IV in a series on cyclopropylarene chemistry.

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We report two new syntheses of (2S,3R)-2-(2Z,5Z-octadienyl)-3-nonyloxirane, the main sex pheromone component of the pink moth, Lymantria mathura. The key step in the first route was the construction of (Z,Z)-1-bromo-1,4-heptadiene (6), which was coupled in the final step with 2-iodomethyl-3-nonyloxirane 4 via a Grignard reaction. The second approach employed alkylation of 1,4-heptadiynyllithium with epoxy triflates 7 in ether/hexane and provided the pheromone in >/=37% overall yield from alcohol 2. The 4:1 ratio of pheromone enantiomers, reportedly the most attractive to pink moth males, can be directly crafted from appropriately selected Sharpless asymmetric epoxidation conditions.

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