Journal of Organic Chemistry p. 2115 - 2121 (1993)
Update date:2022-08-03
Topics:
Glover, Stephen A.
Warkentin, John
Aryl radicals from N-alkyl-N-(2-bromobenzyl)-1-cyclohexenylamine 2 and N-alkyl-N-(2-bromobenzyl)cyclopentenylamine 11 cyclize readily onto the enamine double bond by 6-endo and 5-exo closure.In the case of 2, 6-endo cyclization is the major pathway; however, the 6-endo to 5-exo ratio is dependent upon the N-alkyl substituent.In both cases, the dominant isomer from 6-endo cyclization is the cis isomer.For 2a in toluene, values of k6-endo and k5-exo at 80 deg C were 4.6 x 108 s-1 and 1.5 x 108 s-1, respectively.
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Doi:10.1002/hlca.19490320331
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(2018)Doi:10.1021/om030414b
(2003)Doi:10.1021/acs.orglett.1c00133
(2021)Doi:10.1021/jo01155a006
(1949)Doi:10.1007/BF00945332
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