Intramolecular nucleophilic participation. IX. Solvolysis of o-and p-thiolcarbophenoxybenzyl bromides

SS Friedrich, LJ Andrews…

Index: Friedrich,S.S. et al. Journal of Organic Chemistry, 1972 , vol. 37, # 19 p. 3007 - 3009

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Abstract

In 80% aqueous dioxane o-thiolcarbophenoxybenzyl bromide hydrolyzes significantly faster than does its para isomer (8.11 times at 65'). In acetic acid at 85'the ortho/para solvolysis rate constant ratio is exceptionally high (534) when compared with that for the o-and p- methoxybenzyl bromides (0.0017 at SO0), a system in which ortho substituent participation does not occur. The high reactivity of o-thiolcarbophenoxybenzyl bromide is attributed to ...