Competitive Elimination-Substitution Reactions. Some Dramatic Differences between Bromides and Tosylates

P Veeravagu, RT Arnold…

Index: Veeravagu,P. et al. Journal of the American Chemical Society, 1964 , vol. 86, p. 3072 - 3075

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Citation Number: 30

Abstract

Typical examples of primary alkyl bromides and tosylates were treated with alkosides under preparative conditions. Vndcr conditions that usually lead to elimination rather than substitution, tosylates gave surprisingly good yields of substitution products while the corresponding bromides underwent predominantly the elirnination reaction This sharp difference betlveen bromides and tosylates can be of enormous significance in thc ...