Journal of the Chemical Society. Perkin transactions II p. 17 - 24 (1986)
Update date:2022-08-05
Topics:
Hutton, Alan T.
Modro, Tomasz A.
Niven, Margaret L.
Scaillet, Sonia
1,3-Dimethyl-2-methylamino-1,3,2-diazaphospholidine-2,4,5-trione (1b) has been synthesized, and its solvolytic behaviour and X-ray crystal structure determined.Methanolysis of (1b) gives products of the cleavage of both imide P-N bonds, indicating that the ring opening in (1b) is much slower than the second P-N cleavage in the ring-opened intermediate.The low reactivity of (1b) is correlated with the small size (92.3 deg) of the endocyclic N-P-N angle, which suggests that not much energy is released upon the formation of the PV trigonal bipyramidal adduct.The molecular structure of (1b) reveals a high degree of coplanarity of the phospholidine ring with both imide N-methyl groups and both carbonyl oxygen atoms.The geometry indicates that the endocyclic nitrogen atoms in (1b) are involved in the resonance interactions not only with the adjacent carbonyl groups, but also with the phosphoryl centre. 1,3-Dimethyl-2-phenoxy-1,3,2-diazaphospholidine-2,4,5-trione (1a) has been found to react with p-anisidine or ammonia exclusively at the phosphorus atom.In the reaction with p-anisidine both P-O bond cleavage (displacement of phenol) and ring P-N bond cleavage products were obtained; this is interpreted in terms of pseudorotation of the initially formed PV intermediate.Ammonia reacts with (1a) giving exclusively the ring-retained, P-OPh bond cleavage products.Our aminolysis results for (1a) contrast with those reported in the literature.
View MoreVanderArk International Limited
Contact:86-10-82437576
Address:Qing He
Yueyang Hudex Pharmaceuticals Ltd.
Contact:0730-8748800
Address:Wujiang Bridge，Yueyang Economy & Technology Development Zone
Improve Medical Technology(Nanxiong) Co., Ltd
Contact:86-751-3836997
Address:No.33, Pingan First Road, Fine Chemical Industry Base, Nanxiong City, Shaoguan, Guangdong, China
Weifang Adde Economic And Trade Co.,LTD.
Contact:86-536-8885548
Address:Room 1402,Wanda Plaza B Block,No.958,Yuanfei Road,Kuiwen District
Lianyungang Ningkang Chemical Co., Ltd
Contact:.+86-518-88588008
Address:http://www.chemnk.com
Doi:10.1080/00397910701862931
(2008)Doi:10.1039/c4ra14173c
(2015)Doi:10.1016/j.tetlet.2008.02.057
(2008)Doi:10.1007/s11224-020-01617-6
(2021)Doi:10.1021/acs.orglett.9b01386
(2019)Doi:10.1021/ol0493711
(2004)
