THE REACTIVITY OF OXYGEN NUCLEOPHILES WITH ARYL RADICALS IN THE S(RN)1 MECHANISM

被引:12
作者
BAUMGARTNER, MT [1 ]
PIERINI, AB [1 ]
ROSSI, RA [1 ]
机构
[1] UNIV NACL CORDOBA,FAC CIENCIAS QUIM,DEPT QUIM ORGAN,SUC 16,RA-61 CORDOBA,ARGENTINA
关键词
D O I
10.1016/S0040-4039(00)74201-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The photostimulated reaction of 2-naphthoxide ions 1 with o-dihalobenzenes in liquid ammonia gives the halosubstituted product 4 and the cyclized substituted product 5. This is the first report about the coupling of an aromatic sigma-radical with an oxygen functionality in the chain propagation cycle of the S(RN)1 mechanism.
引用
收藏
页码:2323 / 2326
页数:4
相关论文
共 17 条
[1]   SRN1 STUDIES .23. COUPLING OF IODONAPHTHALENES WITH NAPHTHOXIDE IONS UNDER SRN1 CONDITIONS - SYNTHESIS OF UNSYMMETRICAL BINAPHTHYL DERIVATIVES [J].
BEUGELMANS, R ;
BOISCHOUSSY, M ;
TANG, Q .
TETRAHEDRON LETTERS, 1988, 29 (14) :1705-1708
[2]   SRN1 REACTIONS .22. PHENOXIDE AND NAPHTHOXIDE IONS AS NUCLEOPHILES FOR SRN1 REACTIONS - SYNTHESIS OF BIPHENYL AND PHENYLNAPHTHYL DERIVATIVES [J].
BEUGELMANS, R ;
BOISCHOUSSY, M .
TETRAHEDRON LETTERS, 1988, 29 (11) :1289-1292
[3]   REACTIVITY OF SUBSTITUTED ALIPHATIC NITRO-COMPOUNDS WITH NUCLEOPHILES [J].
BOWMAN, WR .
CHEMICAL SOCIETY REVIEWS, 1988, 17 (03) :283-316
[4]   RADICAL-INDUCED DEIODINATION OF ARYL IODIDES IN ALKALINE METHANOL [J].
BUNNETT, JF ;
WAMSER, CC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (25) :6712-&
[5]   ON MECHANISMS OF DEDIAZONIATION AND OTHER AROMATIC DENITROGENATION REACTIONS INDUCED BY SODIUM METHOXIDE IN METHANOL [J].
BUNNETT, JF ;
TAKAYAMA, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (19) :5173-&
[6]   REACTIONS OF RADICAL ANIONS .I. CLEAVAGE OF RADICAL ANION OF DIBENZOFURAN [J].
EVANS, AG ;
ROBERTS, PB ;
TABNER, BJ .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1966, (03) :269-&
[7]   QUANTITATIVE MODELING OF PROXIMITY EFFECTS ON ORGANIC-REACTIVITY [J].
HOUK, KN ;
TUCKER, JA ;
DORIGO, AE .
ACCOUNTS OF CHEMICAL RESEARCH, 1990, 23 (04) :107-113
[8]   Polarographically controlled syntheses, with particular reference to organic chemistry [J].
Lingane, JJ ;
Swain, CG ;
Fields, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1943, 65 :1348-1353
[9]   SRN1 C-ARYLATION OF POTASSIUM ARYLOXIDES BY ARYLAZO PHENYL OR TERT-BUTYL SULFIDES IN DMSO [J].
PETRILLO, G ;
NOVI, M ;
DELLERBA, C ;
TAVANI, C ;
BERTA, G .
TETRAHEDRON, 1990, 46 (23) :7977-7990
[10]   REGIOCHEMISTRY OF THE COUPLING OF ARYL RADICALS WITH NUCLEOPHILES DERIVED FROM THE NAPHTHYL SYSTEM - EXPERIMENTAL AND THEORETICAL-STUDIES [J].
PIERINI, AB ;
BAUMGARTNER, MT ;
ROSSI, RA .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :580-586