Nucleophilic cleavage of 1-oxo-2, 8-disubstituted-2, 5, 8-triaza-1λ 5-phosphabicyclo [3.3. 0] octanes: a new route to eight-and five-membered heterocyclic systems

Z He, S Laurens, XY Mbianda, AM Modro…

Index: He, Zhengjie; Laurens, Susan; Mbianda, Xavier Y.; Modro, Agnes M.; Modro, Tomasz A. Journal of the Chemical Society. Perkin Transactions 2, 1999 , # 11 p. 2589 - 2596

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Abstract

Five 1-oxo-2, 8-disubstituted-2, 5, 8-triaza-1λ5-phosphabicyclo [3.3. 0] octanes 1 have been prepared and the nucleophilic cleavage of one of their P–N bonds has been studied. The acid-catalyzed alcoholysis involves in each case the cleavage of the P–N (5) bond, yielding the eight-membered monocyclic diamides 2. In the base-catalyzed reaction, the N (2), N (8)- dialkyl substituted substrates 1 yielded the same products 2, while for the N (2), N (8)- ...