Formal transfers of hydride from carbon-hydrogen bonds. Thermolysis of 2, 3-dihydro-2-(2-hydroxyphenyl)-1, 3-dimethyl-1H-benzimidazole

F Montgrain, SM Ramos, JD Wuest

Index: Montgrain, France; Ramos, Socorro M.; Wuest, James D. Journal of Organic Chemistry, 1988 ,  vol. 53,  # 7  p. 1489 - 1492

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Citation Number: 17

Abstract

In 2, 3-dihydro-2-(2-hydroxyphenyl)-l, 3-dimethyl-l~-benzimidazole (3), the acidic hydrogen of a phenolic oxygen-hydrogen bond is near a carbon-hydrogen bond activated as a donor of hydride by two adjacent lone pairs in a dihydro aromatic ring. This juxtaposition does not promote the formation of molecular hydrogen. Instead, thermolysis of compound 3 appears to lead to tautomerization of the hydroxyphenyl group and heterolysis of the carbon- ...