Relative conjugative abilities of three-membered-ring heterocycles with benzene based on carbon-13 and nitrogen-15 NMR

…, JA Hashmall, AP Borsetti, SA Turujman

Index: Crist, DeLanson R.; Jordan, Guy J.; Moore, Donald W.; Hashmall, Joseph A.; Borsetti, Arnold P.; Turujman, Saleh A. Journal of the American Chemical Society, 1983 , vol. 105, # 13 p. 4136 - 4142

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Citation Number: 20

Abstract

Abstract: The conjugative ability of various three-membered rings with benzene was investigated by observing the sensitivity of@-carbon I3C chemical shifts to para substituents. These Hammett p values were 2.0, 1. 5, 1. O, and 0.9 ppm for arylcyclopropanes, N-methyl-2- arylaziridines, phenyloxiranes, and N, N-dimethyl-2-arylaziridinium fluorosulfonates, respectively. These values were intermediate to ones for para-substituted styrenes (6.5 ...