Symmetrical intermediates in C9H12 biradical rearrangements. Possible intervention of an organic tetraradical

L McElwell-White, DA Dougherty

Index: McElwee-White, Lisa; Dougherty, Dennis A. Journal of the American Chemical Society, 1982 , vol. 104, # 17 p. 4722 - 4724

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Citation Number: 8

Abstract

As a test for this precedented route to 5, we prepared 2b with completely stereospecific exo- deuterium labeling (Scheme I). 9 Cleavage of the Cl-C5 bond requires that the deuteriums of 2b end up in the aliphatic CH2's of 5. However, any intervention by 1 would make all CH2 groups equivalent and would thus produce aliphatic (A) and vinylic (V) deuteriums in 5. As shown in Table 11, sensitized photolysis of 2b gives both 5-A and 5-V. The four aliphatic ...