Hydration with Mercuric Acetate and the Reduction with 9-BBN-H of 2-(1-Alkenyl)-4, 6-dimethyl-s-triazines

…, LS Hurlbut, R Watson-Clark, DE Harwell

Index: Nyquist, H. LeRoy; Beeloo, Edward A.; Hurlbut, Lydia S.; Watson-Clark, Rachel; Harwell, David E. Journal of Organic Chemistry, 2002 , vol. 67, # 10 p. 3202 - 3212

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Citation Number: 4

Abstract

Oxymercuration-demercuration of a double bond in conjugation with the 4, 6-dimethyl-s- triazin-2-yl substituent as in alkenes 1a, b gave anti-Markovnikov regioselectivity, which is explained by the electron-withdrawing nature of the triazinyl substituent. However, hydroboration of the conjugated alkenes with 9-BBN-H gave the corresponding alkanes 5a- c under normal workup conditions with or without oxidation. With time and without workup ...