Ap. Laws et al., LARGE RATE ENHANCEMENT FOR THE HYDROLYSIS OF A 4-MEMBERED RING PHOSPHONAMIDATE, Journal of the Chemical Society, Chemical Communications, (10), 1994, pp. 1223-1224
Unlike beta-lactams a four-membered cyclic 1,2-azaphosphetidine shows
enhanced hydrolytic reactivity compared with an acyclic analogue; the
cyclic phosphonamidate 3 undergoes hydroxide-ion catalysed hydrolysis
in water with endocyclic P-N fission; a corresponding acyclic derivati
ve hydrolyses with P-O fission in basic solution, the rate difference
between the cyclic and acyclic structures for P-N fission is greater t
han 5 x 10(8).