The stereochemistry of alkylation of 7-alkyl-7.12-dihydropleiadene anions
作者： Zbigniew Marcinow , Peter W. Rabideau
DOI: 10.1016/S0040-4039(01)81599-9
关键词: Inversion barrier 、 Chemistry 、 Alkyl 、 Alkylation 、 Deprotonation 、 Stereochemistry 、 Carbanion
摘要: Abstract Attempts to rationalize the stereochemistry resulting from alkylation of 7-R-12-metallo-7,12-dihydropleiadene geometries neutral precursors were not successful. A new model is suggested.
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sci-hub.se 参考文章(26)
Ronald G. Harvey, Charles C. Davis, Metal-ammonia reduction. VI. Stereospecific alkylation of the 9-alkyl-9,10-dihydro-10-anthryl carbanion Journal of Organic Chemistry. ,vol. 34, pp. 3607- 3609 ,(1969) , 10.1021/JO01263A084
R.G. Harvey, L. Arzadon, Metal-ammonia reduction—V Tetrahedron. ,vol. 25, pp. 4887- 4894 ,(1969) , 10.1016/S0040-4020(01)83029-5
Michele Daney, Henry Bouas-Laurent, Bernard Calas, Louis Giral, Nicole Platzer, Reactivite des carbanions benzyliques Journal of Organometallic Chemistry. ,vol. 188, pp. 277- 291 ,(1980) , 10.1016/S0022-328X(00)83040-5
Peter W. Rabideau, The conformational analysis of 1,4-cyclohexadienes: 1,4-dihydrobenzenes, 1,4-dihydronaphthalenes, and 9,10-dihydroanthracenes Accounts of Chemical Research. ,vol. 11, pp. 141- 147 ,(1978) , 10.1021/AR50124A003
S. Bank, J. Bank, M. Daney, B. Labrande, H. Bouas-Laurent, Reactivity of benzylic carbanions. 4. Kinetic studies of reactions of alkyl halides with 9-alkyl-10-lithio-9,10-dihydroanthracenes and diphenylmethyllithium. The relationship of reaction rates to product stereochemistry Journal of Organic Chemistry. ,vol. 42, pp. 4058- 4061 ,(1977) , 10.1021/JO00445A015
Daniel H. O'Brien, Charles R. Russell, Alan J. Hart, The solvation of diphenylmethyl carbanions using variable temperature carbon-13 magnetic resonance Journal of the American Chemical Society. ,vol. 98, pp. 7427- 7429 ,(1976) , 10.1021/JA00439A056
Peter P. Fu, Ronald G. Harvey, Johanthan W. Paschal, Peter W. Rabideau, Stereochemistry of 9,10-dialkyl-9,10-dihydroanthracene and 9-alkyl-10-lithio-9,10-dihydroanthracene Journal of the American Chemical Society. ,vol. 97, pp. 1145- 1153 ,(1975) , 10.1021/JA00838A031
Michele Daney, Rene Lapouyade, Monique Mary, Henri Bouas-Laurent, Reactivite des carbanions benzyliques : II. Stereochimie d'alcoylation des ethyl et isopropyl-9 lithio-10 dihydro-9,10 anthracenes☆ Journal of Organometallic Chemistry. ,vol. 92, pp. 267- 274 ,(1975) , 10.1016/S0022-328X(00)85677-6
Michele Daney, Rene Lapouyade, Reactivite des carbanions benzyliques Journal of Organometallic Chemistry. ,vol. 172, pp. 385- 390 ,(1979) , 10.1016/S0022-328X(00)92310-6
Douglas J. Raber, Linda E. Hardee, Peter W. Rabideau, Kenny B. Lipkowitz, Structure and conformation of dihydroaromatic compounds. 1-Alkyl-1,4-dihydrobenzenes, 1-alkyl-1,4-dihydronaphthalenes, and 9-alkyl-9,10-dihydroanthracenes Journal of the American Chemical Society. ,vol. 104, pp. 2843- 2847 ,(1982) , 10.1021/JA00374A025