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Organic Chemistry

Synthesis of Verbenols and Related Alcohols and Their PMR Spectra with Shift Reagent

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Pages 1967-1974 | Received 24 May 1979, Published online: 09 Sep 2014
 

Abstract

In connection with our investigation on the structure-activity relationships of the American cockroach sex pheromone mimic, (+)-trans-verbenyl acetate, a number of alcohols having 6,6-dimethylbicyclo[3, 1. l]heptane skeleton were synthesized, and measured their PMR spectra in the presence of the shift reagent, Eu(dpm)3. The induced shifts of the 6, 6-gem-dimethyl protons and α-proton at the C–7 guided us to distinction between cis- and trans-alcohol. The configuration of secondary methyl groups was discussed from the induced shift values of the methyl protons.

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