Insights into regioselective oxy (-O-) and imino (-NH-) group insertions of 3-nortricyclanone

MG Rosenberg, U Haslinger…

Index: Rosenberg, Murray G.; Haslinger, Ulrike; Brinker, Udo H. Journal of Organic Chemistry, 2002 , vol. 67, # 2 p. 450 - 456

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Citation Number: 9

Abstract

Lactam 4-azatricyclo [3.2. 1.02, 7] octan-3-one (16a) was proven to be formed in a previously reported reaction that claimed production of lactam 3-azatricyclo [3.2. 1.02, 7] octan-4-one (17a). In a related reaction, bicyclo [3.1. 0] hex-2-ene-endo-6-carbonitrile (15), lactam (16a), and novel hydroxycarbonitriles 19-21 were selectively formed when 3- nortricyclanone (1) was treated with aqueous hydroxylamine-O-sulfonic acid (HOSA). ...