Exploratory investigations probing a preparatively versatile, pyridinium salt photoelectrocyclization-solvolytic aziridine ring opening sequence

R Ling, M Yoshida, PS Mariano

Index: Ling, Rong; Yoshida, Mutsuo; Mariano, Patrick S. Journal of Organic Chemistry, 1996 , vol. 61, # 13 p. 4439 - 4449

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Citation Number: 164

Abstract

A novel pyridinium salt photoelectrocyclization-nucleophilic bicyclic aziridine ring opening reaction sequence has been investigated in order to determine its preparative potential. N- Alkylpyridinium perchlorates were found to undergo photoinduced electrocyclization upon irradiation in nucleophilic solvents, such as H2O and MeOH, to efficiently produce 6-alkyl-6- azabicyclo [3.1. 0] hex-2-en-4-yl alcohols and ethers. The bicyclic aziridine photoproducts ...