STUDIES ON d-ORBITAL CONJUGATION. I. THE ABSENCE OF A THROUGH-CONJUGATION EFFECT IN SOME SULFONE CARBANIONS

R Breslow, E Mohacsi

Index: Breslow,R.; Mohacsi,E. Journal of the American Chemical Society, 1961 , vol. 83, p. 4100 - 4101

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Citation Number: 13

Abstract

It is interesting that we find the PIC, of V to be 11.5 while that of VI is greater than 13. Thus the order of stability of these systems is reversed when the carbethoxyl group is missing. This may reflect a changed hybridization at carbon when the substituent no longer demands sp2-p hybridization, and we are further investigating systems of this type. However, it is clear from our results that a large extra conjugation effect, such as was predicted from the Koch ...