LARGE RATE ENHANCEMENT FOR THE HYDROLYSIS OF A 4-MEMBERED RING PHOSPHONAMIDATE

被引:6
作者
LAWS, AP [1 ]
STONE, JR [1 ]
PAGE, MI [1 ]
机构
[1] UNIV HUDDERSFIELD, DEPT CHEM & BIOL SCI, HUDDERSFIELD HD1 3DH, W YORKSHIRE, ENGLAND
关键词
D O I
10.1039/c39940001223
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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 derivative hydrolyses with P-O fission in basic solution, the rate difference between the cyclic and acyclic structures for P-N fission is greater than 5 x 10(8).
引用
收藏
页码:1223 / 1224
页数:2
相关论文
共 12 条
[1]   SYNTHESIS OF 1,2-AZAPHOSPHETIDINES [J].
AFARINKIA, K ;
CADOGAN, JIG ;
REES, CW .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (03) :285-287
[2]   LOW-COORDINATED PHOSPHORUS-COMPOUNDS .10. SYNTHESIS OF A 1,3-AZAPHOSPHETIDINE WITH EXOCYCLIC (PC) DOUBLE-BOND [J].
APPEL, R ;
HALSTENBERG, M ;
KNOCH, F ;
KUNZE, H .
CHEMISCHE BERICHTE-RECUEIL, 1982, 115 (06) :2371-2373
[3]   ACYL AND ALKYLIDENE PHOSPHINES .13. MOLECULAR AND CRYSTAL-STRUCTURE OF 2,4-DI(TERT-BUTYL)-2,4-BIS(TRIMETHYLSILOXY)-1,3-DIPHOSPHETANE [J].
BECKER, G ;
UHL, W .
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1981, 475 (04) :35-44
[4]   THE MECHANISMS OF HYDROLYSIS OF THE GAMMA-LACTAM ISATIN AND ITS DERIVATIVES [J].
CASEY, LA ;
GALT, R ;
PAGE, MI .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (01) :23-28
[5]   CRYSTAL STRUCTURE OF A WITTIG INTERMEDIATE CONTAINING A 4-MEMBERED RING . 4,4-BIS(TRIFLUOROMETHYL)2,2,2-TRIPHENYL-3-(TRIPHENYLPHOSPHORANYLIDENE)-1,2-OXAPHOSPHETANE [J].
CHIOCCOLA, G ;
DALY, JJ .
JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1968, (03) :568-+
[6]   HYDROLYSIS RATE DIFFERENCE BETWEEN CYCLIC AND ACYCLIC PHOSPHATE-ESTERS - SOLVATION VERSUS STRAIN [J].
DEJAEGERE, A ;
KARPLUS, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) :5316-5317
[7]   THE MECHANISMS OF REACTIONS OF BETA-LACTAM ANTIBIOTICS [J].
PAGE, MI .
ADVANCES IN PHYSICAL ORGANIC CHEMISTRY, 1987, 23 :165-270
[8]  
PAGE MI, 1993, CHEM BETA LACTAMS, P79
[9]   O-18 EXCHANGE ACCOMPANYING THE BASIC HYDROLYSIS OF PRIMARY, SECONDARY, AND TERTIARY TOLUAMIDES .2. THE IMPORTANCE OF AMINE LEAVING ABILITIES FROM THE ANIONIC TETRAHEDRAL INTERMEDIATES [J].
SLEBOCKATILK, H ;
BENNET, AJ ;
KEILLOR, JW ;
BROWN, RS ;
GUTHRIE, JP ;
JODHAN, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (23) :8507-8514
[10]  
THATCHER GRJ, 1989, ADV PHYS ORG CHEM, V25, P99