REACTION OF ALLYL IMINOPHOSPHORANES WITH KETENES AND ACYL CHLORIDES - ONE-POT PREPARATION OF 4-PENTENENITRILES

被引：19

作者：

MOLINA, P

ALAJARIN, M

LOPEZLEONARDO, C

ALCANTARA, J

机构：

[1] Departamento de Química Orgánica, Facultad de Química, Universidad de Murcia, E-30071 Murcia, Campus de Espinardo

来源：

TETRAHEDRON | 1993年 / 49卷 / 23期

关键词：

D O I：

10.1016/S0040-4020(01)81880-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

One-pot conversion of allyl azides into 4-pentenenitriles 4 is achieved by sequential treatment of allyl azides with triphenylphosphine and the corresponding ketene under mild and neutral conditions. On the other hand, allyl iminophosphoranes and related react with arylacetic acid chlorides to give unexpectedly the phosphonium salts 5 which by treatment with base and then heating lead to 4-pentenenitriles 9.

引用

页码：5153 / 5168

页数：16

共 26 条

[1]

BALDERMAN D, 1978, SYNTHESIS-STUTTGART, P24

[2] REACTIONS OF CYCLOPROPYL SULFONATES WITH NUCLEOPHILES - SN2 DISPLACEMENTS AT CYCLOPROPANES WITH INVERSION [J].

BANERT, K .

CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (04) :1564-1574

[3] HALOGENATED KETENES .9. KETENE CARBODIIMIDE CYCLOADDITIONS [J].

BRADY, WT ;

DORSEY, ED ;

PARRY, FH .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (10) :2846-&

[4] PREPARATION OF 4-PENTENENITRILES AND 3,4-PENTADIENENITRILES FROM N-(2-ALKENYL)- AND N-(2-ALKNYL)AMIDES [J].

BRANNOCK, KC ;

BURPITT, RD .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (08) :2564-&

[5] RELATIVELY STABLE N-BENZHYDRYLKETENE AND N-BENZYLDIARYLKETENE IMINES AND THEIR CONVERSION TO CYANODIARYLMETHANES VIA AN ISOLABLE RADICAL [J].

CLARKE, LF ;

HEGARTY, AF ;

ONEILL, P .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (01) :362-366

[6] REARRANGEMENT OF ALLYLIC AZIDES [J].

GAGNEUX, A ;

WINSTEIN, S ;

YOUNG, WG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (22) :5956-5957

[7] AQUEOUS INTERMOLECULAR DIELS-ALDER CHEMISTRY - REACTION OF (E)-2,4-PENTADIENYL AMMONIUM-CHLORIDE AND RELATED AMMONIUM-SALTS WITH DIENOPHILES IN WATER [J].

GRIECO, PA ;

GALATSIS, P ;

SPOHN, RF .

TETRAHEDRON, 1986, 42 (11) :2847-2853

[8] SYNTHETIC METHODS .22. SYNTHESIS OF ALKYL AZIDES WITH A POLYMERIC REAGENT [J].

HASSNER, A ;

STERN, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (05) :478-479

[9] THERMALLY LABILE KETENIMINES FROM TRIPHENYLPHOSPHINALKYLIMINES [J].

LEE, KW ;

SINGER, LA .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (25) :3780-3781

[10] FACILE 1,3-REARRANGEMENT OF KETENIMINES TO NITRILES - STEREOCHEMICAL OBSERVATIONS ON A CAGED CHIRAL RADICAL PAIR [J].

LEE, KW ;

HOROWITZ, N ;

WARE, J ;

SINGER, LA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (08) :2622-2627

← 1 2 3 →