The Journal of Organic Chemistry

Regiochemical control of the addition of aryl selenols and aryl thiols to the triple bond of arylpropiolates. Synthesis of seleno-and thioflavones and seleno-and …

DH Wadsworth, MR Detty

Index: Wadsworth, Donald H.; Detty, Michael R. Journal of Organic Chemistry, 1980 , vol. 45, # 23 p. 4611 - 4615

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Citation Number: 77

Abstract

Addition of aryl selenols and aryl thiols to arylpropiolates under basic conditions followed by saponification gave exclusively P-substituted cinnamates of predominant 2 stereochemistry. Neat solutions of aryl selenols or aryl thiols and arylpropiolates after saponification gave a- substituted cinnamates of presumed Z stereochemistry. The latter reactions are assumed to be radical additions. Cyclization of the cinnamates with phosphorus pentoxide- ...