The Conversion of 1,3-Cyclooctadiene to 1-Vinylcyclohexene |
| |
Authors: | J C Duggan Harold Weingarten |
| |
Institution: | Central Research Dept. , Monsanto Co. , St. Louis, Mo., 63166, U.S.A. |
| |
Abstract: | Meroquinene (1), a key degradation product of quinine and an important intermediate in the preparation of the cinchona and other alkaloids,1 has only recently been synthesized 2 even though attempts were made at its preparation for over thirty years. These early attempts were frustrated primarily by the difficulty encountered in the introduction of a potential vinyl group onto a piperidine ring. Alkylation of 3-car-bethoxy-N-benzoyl-4-piperidone (2) with either phenoxyethyl chloride3 or dimethylaminoethyl chloride (3)4 resulted in exclusive formation of the O-alkylated product, even though alkylation of the presumably analogous 2-carbethoxycyclohexanone with 3 gave nearly equal amounts of C- and O- alkylated materials.4 The use of other piperidone derivatives in this reaction was precluded by the report that attempts to alkylate 3-car-bethoxy-N-alkyl-4-piperidones gave only the quaternary nitrogen product.5 |
| |
Keywords: | |
|
|