Evidence for electron transfer in reactions of nucleophiles with optically active alkyl halides. A challenge to the SN2 transition state.
作者： E.C Ashby , Tung N Pham
DOI: 10.1016/S0040-4039(00)95466-2
关键词:
摘要: Abstract A variety of nucleophiles have been used in a study reactions with optically active 2-halooctanes DMF order to detect the occurrence an electron transfer pathway.
elsevier.com
sci-hub.se 参考文章(16)
E. C. Ashby, R. N. DePriest, Wei Yang Su, Electron transfer in the reactions of alkyl halides with sodium trimethylstannate Organometallics. ,vol. 3, pp. 1718- 1727 ,(1984) , 10.1021/OM00089A021
E. C. Ashby, Robert DePriest, Evidence for inversion of configuration in reactions involving radical processes Journal of the American Chemical Society. ,vol. 104, pp. 6144- 6146 ,(1982) , 10.1021/JA00386A064
Joseph San Filippo, Louis J. Romano, A convenient preparation of optically active 2-halooctanes and related compounds Journal of Organic Chemistry. ,vol. 40, pp. 1514- 1515 ,(1975) , 10.1021/JO00898A036
Mikhail S. Alnajjar, Henry G. Kuivila, Solvent and counterion effects on the stereochemistry and the competition between electron-transfer and SN2 mechanisms in the reactions of (trimethylstannyl)alkalis with bromides Journal of the American Chemical Society. ,vol. 107, pp. 416- 423 ,(1985) , 10.1021/JA00288A023
E.C. Ashby, R.N. DePriest, T.N. Pham, Concerning the reduction of alkyl halides by LiAlH4 evidence that AlH3 produced in situ is the one electron transfer agent. Tetrahedron Letters. ,vol. 24, pp. 2825- 2828 ,(1983) , 10.1016/S0040-4039(00)88034-X
E. C. Ashby, W. S. Park, A. B. Goel, Wei Yang Su, Single electron transfer in reactions of alkyl halides with lithium thiolates Journal of Organic Chemistry. ,vol. 50, pp. 5184- 5193 ,(1985) , 10.1021/JO00225A041
Eugene C. Ashby, Wei Yang. Su, Tung N. Pham, Evidence for electron transfer in the reaction of (trimethylstannyl)sodium with primary alkyl halides Organometallics. ,vol. 4, pp. 1493- 1501 ,(1985) , 10.1021/OM00128A001
Eugene C. Ashby, Robert N. DePriest, Anil B. Goel, Electron transfer in the reduction of primary halides by metal hydrides Tetrahedron Letters. ,vol. 22, pp. 1763- 1766 ,(1981) , 10.1016/S0040-4039(01)90433-2
E. C. Ashby, Bernd Wenderoth, Tung N. Pham, Won Suh Park, Evidence for single electron transfer in the reduction of organic halides by lithium triethylborohydride Journal of Organic Chemistry. ,vol. 49, pp. 4505- 4509 ,(1984) , 10.1021/JO00197A036
E. C. Ashby, Tung N. Pham, The use of 5-halocyclooctenes as a radical probe. Reactions with lithium aluminum hydride Journal of Organic Chemistry. ,vol. 51, pp. 3598- 3602 ,(1986) , 10.1021/JO00369A009