References
- Hamon , D. P. G. and Spurr , P. R. Synthesis , 1981 873
- Nishiyama , H. , Sasaki , M. and Itoh , K. Chemistry Lett. , 1981 1363
- Similar intra- and intermolecular dimerizations have been reported.
- Janitschke , L. and Kreiser , W. Synthsis , 1976 314
- McDonald , R. N. and Reitz , R. R. 1972 . J. Org. Chem. , 37 : 2418 Application of this reaction condition to intermolecular reaction did not give satisfactory results.
- The oxidative C-C single bond coupling of ester anions have been reported.
- Saegusa , T. , Ito , Y. and Konoike , T. 1975 . J. Amer. Chem. Soc. , 97 : 649
- Ito , Y. , Konoike , T. , Harada , T. and Saegusa , T. 1977 . ibid. , 99 : 1487
- Chung , S. K. and Dunn , L. B. 1983 . J. Org. Chem. , 48 : 1125
- Reaction pathway is uncertain; the addition of cyclohexene or the introduction of oxygen in the reaction mixture of ethyl α-bromopropionate did not give any detectable amount of the adduct having a cyclopropane ring or a C-C single bond coupling product. This result eliminates the intervention of a copper stabilized carbene or copper ate complex6 as a plausible intermediate. Since deuterium take-up of ethyl α-bromopropionate was ca. 39% at -70°C in the presence of LDA and CuI, the reaction would proceed presumably via a pathway involving the substitution-elimination of copper stabilized carbanions to provide maleates mainly
- Kuwajima , I. and Doi , Y. Tetrahedron Lett. , 1972 1163