Synthesis of. beta.-lactams by the photochemical extrusion of sulfur dioxide from 1, 1-dioxo-4-thiazolidinones

MR Johnson, MJ Fazio, DL Ward…

Index: Johnson; Fazio; Ward; Sousa Journal of Organic Chemistry, 1983 , vol. 48, # 4 p. 494 - 499

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Citation Number: 20

Abstract

Photolysis of cis-3, 5-dimethyl-l, l-dioxo-2-phenyl-4-thiazolidinone (through a Vycor filter, in t- BuOH/CH&N) gives cis-1, 3-dimethyl-4-phenyl-2-azetidinone in 43% yield and the corresponding trans P-lactam in 11% yield. Photolysis of tra~-3, 5-dimethyl-1, l-dioxo-2- phenyl-4-thiazolidinone gives lower yields of 0-lactam, with the trans stereoisomer predominating. Thermal reaction of the l, l-dioxo-2-phenyl-4-thiazolidinones gives only the ...