The Journal of Organic Chemistry

Chlorosulfonyl isocyanate addition to bicyclo [2.1. 0] pentane

EJ Moriconi, CP Dutta

Index: Moriconi,E.J.; Dutta,C.P. Journal of Organic Chemistry, 1970 , vol. 35, p. 2443 - 2445

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Citation Number: 6

Abstract

Reduction of 2 with benzenethiol-pyridine (7573, LiAlH4 (45%) and pH-controlled hydrolysis (55%) afforded the more stable, crystalline lactam, 2-aza-3-ketobicyclo [2.1. 0] heptane (5), in which the infrared carbonyl absorption had undergone the precedented red shift to 5.72 p and the exchangeable NH proton made its appearance in the nmr at 6 7.28-6.72. The reaction of 1 in solvents of increasing polarity, ether (0') and methylene chloride (-80 to 75” ...