Tetrahedron

Allenes-41: The addition of thiols to allenyl-and phenylpropynyl-nitrile and the formation of thiazolines and benzothiazoles

SR Landor, PD Landor, ZT Fomum, JT Mbafor

Index: Landor, Stephen R.; Landor, Phyllis D.; Fomum, Z. Tanee; Mbafor, J. Tanyi; Mpango, George W. B. Tetrahedron, 1984 , vol. 40, # 11 p. 2141 - 2149

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Citation Number: 2

Abstract

Thiols add to allenylnitriles to give unconjugated nitriles which may be isomerised to conjugated enesulphide nitriles either at high temperature (200°) or with base. Phenylpropynenitrile gives conjugated adducts directly. Heating the conjugated adducts from aminoethanethiols at> 200° results in 5-exotrig ring closure and elimination of acetonitrile to give thiazolines and benzothiazoles.

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