The Journal of Organic Chemistry

Halogenated ketenes. 38. Cycloaddition of. alpha.,. beta.-unsaturated imines with ketenes to yield both. beta.-and. delta.-lactams

WT Brady, CH Shieh

Index: Brady, William T.; Shieh, C. H. Journal of Organic Chemistry, 1983 , vol. 48, # 15 p. 2499 - 2502

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Citation Number: 56

Abstract

The cycloaddition of various types of cu,@-unsaturated imines with diphenyl-and dichloroketenes yields both (2+ 2) and (4+ 2) cycloaddition products, ie,@-lactams and 6- lactams7 respectively. The cycloaddition products are dependent upon substitution in the imine and the ketene. The 6-lactams derived from dichloroketene are easily dehydrochlorinated to the corresponding 2-pyridones. All of the results are consistent with ...