Preparative Organic Chemistry
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ChemInform Abstract: The Hydrolysis of Azetidinyl Amidinium Salts. Part 1. The Unimportance of Strain Release in the Four-Membered Ring.
First published: September 11, 1990
Abstract
The alkaline hydrolysis of the salts (I), (V), and (VIII) is examined with respect to the effect of structural changes within the amidinium moiety.
ChemInform Abstract
The alkaline hydrolysis of the salts (I), (V), and (VIII) is examined with respect to the effect of structural changes within the amidinium moiety. All except the derivative (Ib) undergo preferential exocyclic C-N bond fission to give β-lactams (IIIa), (VI), and (X) as the major product (kinetics, pH-dependence; for buffer and substituent effects and a detailed mechanism discussion see Part 2., next ref.). Evidence is presented for the formation of tetrahedral intermediates by addition of HO- to the +N=C carbon.
