Synthesis, structure and comparative stability of β-hydrazono, oximino methyl ether and imino boronates

…, HE Sailes, JP Watts, A Whiting

Index: Mears, Richard J.; Sailes, Heien E.; Watts, John P.; Whiting, Andrew Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 19 p. 3250 - 3263

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Citation Number: 23

Abstract

β-Hydrazono and oximino ether boronates have been prepared by the sequential lithiation of the corresponding methyl hydrazone or oxime methyl ether, followed by reaction with an iodomethylboronate ester, typically in the form of the pinacol ester. The resulting products have contrasting hydrolytic stabilities. β-Hydrazono boronates are highly sensitive to intramolecularly catalysed hydrolysis, providing the corresponding β-keto boronates in ...