Cycloaddition reactions of an iminophosphorane bearing the Martin ligand with some double-bond compounds:: syntheses, structures and thermolyses of a 1,3,2λ5-oxazaphosphetidine and a 1,3,2λ5-diazaphosphetidine-4-thione

被引：9

作者：

Kano, N ^{[1
]}

Xing, JH ^{[1
]}

Kawa, S ^{[1
]}

Kawashima, T ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan

来源：

POLYHEDRON | 2002年 / 21卷 / 5-6期

关键词：

iminophosphorane; cycloaddition; four-membered ring compounds; thermolysis; aza-wittig reaction; X-ray analysis;

D O I：

10.1016/S0277-5387(01)01024-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Reactions of an iminophosphorane bearing the Martin ligand (2,4,6-Pr3C6H2)(-C6H4-2-C(CF3)(2)O-)P=NPh 1 with carbonyl compounds and phenyl isothiocyanate gave the corresponding [2 + 2]-cycloadducts, 1,3,2lambda(5)-oxazaphosphetidine 2a and 1,3,2lambda(5)-diazaphosphetidine-4-thione 8a, respectively, whose structures were characterized by X-ray crystallographic analyses. Thermolysis of cycloadduct 2a, which is considered as an intermediate of the aza-Wittig reaction, showed two reactivities giving cyclic phosphinate 4 and imine 5 as well as I and ketone 3, respectively. Thermolysis of 8a afforded not only 1 and phenyl isothiocyanate 7a, but also cyclic thiophosphinate 10 and diphenylcarbodiimide 11a. The formation of 10 and 11a suggests the bond recombination around phosphorus atom of 8a. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：657 / 665

页数：9

共 27 条

[1]

[Anonymous], COMPREHENSIVE HETE B

[2] 1-AMINODIAZAPHOSPHENE, SYNTHESIS, CRYSTAL-STRUCTURE, BONDING PROPERTIES, AND REACTIVITY OF A DERIVATIVE [J].

DRESSLER, U ;

NIECKE, E ;

POHL, S ;

SAAK, W ;

SCHOELLER, WW ;

SCHAFER, HG .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (14) :1086-1087

[3] MONOCYCLIC 1,3,2-LAMBDA-5-OXAZAPHOSPHETANES [J].

FRANCKE, R ;

DAKTERNIEKS, D ;

GABLE, RW ;

HOSKINS, BF ;

ROSCHENTHALER, GV .

CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (03) :922-930

[4] 6-THIA-1-AZA-5-LAMBDA-5-PHOSPHABICYCLO[3.2.0]HEPT-3-ENES AND ISOTHIOCYANATOPHOSPHINE-SULFIDES FROM (METHYLIDENAMINO)PHOSPHINES, CARBON-DISULFIDE, AND ACETYLENE-DERIVATIVE OR ETHYLENE-DERIVATIVE [J].

FULDE, M ;

RIED, W ;

BATS, JW .

HELVETICA CHIMICA ACTA, 1989, 72 (01) :139-146

[5] RECENT ADVANCES IN THE STAUDINGER REACTION [J].

GOLOLOBOV, YG ;

KASUKHIN, LF .

TETRAHEDRON, 1992, 48 (08) :1353-1406

[6] HYDROXYPHOSPHORANES AND PHOSPHORANOXIDE ANIONS - SYNTHESIS, REACTIVITY, AND ACIDITY OF PENTACOORDINATE PHOSPHORUS-ACIDS [J].

GRANOTH, I ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (16) :4618-4621

[7] STRUCTURAL DISTORTIONS OF CYCLIC PHOSPHORANES AND BERRY EXCHANGE COORDINATE - QUANTITATIVE DESCRIPTION [J].

HOLMES, RR ;

DEITERS, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (10) :3318-3326

[8] Synthesis, structure, and thermolysis of pentacoordinate 1,3,2λ5-oxazaphosphetidines:: the intermediates of aza-Wittig reactions [J].

Kano, N ;

Hua, XJ ;

Kawa, S ;

Kawashima, T .

TETRAHEDRON LETTERS, 2000, 41 (27) :5237-5241

[9] Formation and X-ray crystallographic analysis of a 1,2λ5-oxaphosphol-5(2H)-one [J].

Kano, N ;

Xing, JH ;

Kikuchi, A ;

Kawashima, T .

HETEROATOM CHEMISTRY, 2001, 12 (04) :282-286

[10] Synthesis, structure, and thermolysis of N-apical 1,2 lambda(5)-azaphosphetidines with a pentacoordinate P center and the first observation of their N-equatorial pseudorotamers [J].

Kawashima, T ;

Soda, T ;

Okazaki, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (10) :1096-1098

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