The Journal of Organic Chemistry

Carbenes and the oxygen-hydrogen bond: hydroxyalkyl-substituted arylcarbenes

W Kirmse, K Kund

Index: Kirmse, Wolfgang; Kund, Klaus Journal of Organic Chemistry, 1990 , vol. 55, # 8 p. 2325 - 2332

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Citation Number: 25

Abstract

[2-(H ydroxymethyl) phenyl] carbene (4),[2-(hydroxymethy1) phen yl] phenylcarbene (19), and [2-(2-hydroxyethy1) phenyllcarbene (30) have been generated by photolysis of tosylhydrazone or diazo precursors in protic solvents. These carbenes give cyclic ethers (7, 18, 33) competitively with insertion into 0-H bonds of the solvent. For comparison, the analogous benzyl cations (9, 17, 31) have been generated by solvolysis or dediazoniation ...

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