A new general route to N-protonated azomethine ylides from N-(silylmethyl) amidines and-thioamides. Cycloaddition of synthetic equivalents of nitrile ylides

O Tsuge, S Kanemasa, K Matsuda

Index: Tsuge, Otohiko; Kanemasa, Shuji; Matsuda, Koyo Journal of Organic Chemistry, 1986 , vol. 51, # 11 p. 1997 - 2004

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Citation Number: 55

Abstract

OTf-because these heterocumulenes 1-3 are readily prepared in high yields from commercially available (chloromethy1) trimethylsilane via (trimethylsily1) methyl a~ ide. 87~ The reaction of 1-3 with a variety of organometallic reagents smoothly occurred at room temperature in dry ether or THF providing excellent yields of N-((tri-methylsily1) methyl) amidines 4-13 and-thioamides 14-16