Strategic synthesis based on cyclohexadienes: preparation of 2-, 2,3- and 2,4-substituted cyclohexenones; synthesis of (Z)-heneicosa-6-en-11-one
- 1 January 1983
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 1,p. 7-10
- https://doi.org/10.1039/p19830000007
Abstract
The mesomeric anions, generated from 1-methoxycyclohexa-1,4-diene, 1-methoxy-5-methylcyclohexa-1,4-diene, and 1-methoxy-4-methylcyclohexa-1,4-diene with potassium amide in liquid ammonia, have been readily alkylated and the resulting dienes were hydrolysed to yield 2-alkyl-, 2,3-dialkyl- and 2,4-dialkyl-cyclohex-2-enones in good yield. Arylation of the above mesomeric anions followed by hydrolysis afforded 2-arylcyclohex-2-enones in addition to substituted biphenyls. A new and efficient synthesis of the male sex attractant of the Douglas Fir Tussock Moth, (Z)-heneicosa-6-en-11-one is described using the above methodology.This publication has 2 references indexed in Scilit:
- The synthesis of insect sex phermonesTetrahedron, 1977
- Synthesis of aliphatic insect pheromones from alicyclic starting materialsTetrahedron, 1977