SOLVOLYSIS OF N-CHLORO-1,4-DIHYDRO-1,4-IMINONAPHTHALENES(7-AZABENZONORBORNADIENES) - DEPENDENCE OF THE REARRANGEMENT PATHWAY ON THE CONFIGURATION AT NITROGEN

被引：10

作者：

DURRANT, ML ^{[1
]}

MALPASS, JR ^{[1
]}

机构：

[1] UNIV LEICESTER,DEPT CHEM,LEICESTER LE1 7RH,LEICS,ENGLAND

来源：

TETRAHEDRON | 1995年 / 51卷 / 25期

关键词：

D O I：

10.1016/0040-4020(95)00336-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Chloro- derivatives of the 1,4-dihydro-1,4-iminonaphthalene (7-azabenzonorbonradiene) ring system undergo silver (I)-assisted rearrangement with participation of etheno- (syn-chloro- series) or benzo- (anti-chloro- series) pi-electrons. The high barriers to inversion at nitrogen together with some control over the ratio of invertomers allow observation of a different reaction pathway for each invertomer when reactions are performed at low temperatures; approaches which allow selection of the benzo- participation route (giving 6,7-benzo-derivatives of the 1-azabicyclo[3.2.0]hept-3-ene ring system) are described.

引用

页码：7063 / 7076

页数：14

共 30 条

[1] PERICYCLIC SYNTHESIS AND EXPLORATORY PHOTOCHEMISTRY OF POTENTIALLY DIRECT PROGENITORS OF UNRESTRICTED HETERO[11]ANNULENE SYSTEM [J].

ANASTASSIOU, AG ;

REICHMANIS, E ;

GIRGENTI, SJ ;

SCHAEFERRIDDER, M .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (02) :315-322

[2] TRANSANNULAR CYCLIZATION OF CYCLO-OLEFINIC N-CHLORO-AMINES - SYNTHESIS OF AZABICYCLIC COMPOUNDS [J].

BASTABLE, JW ;

RIDDELL, WD ;

HOBSON, JD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (17) :2205-&

[3] N-15 NUCLEAR-MAGNETIC-RESONANCE STUDIES OF AZABICYCLES - UNUSUAL DESHIELDING OF NITROGEN IN THE 7-AZABICYCLO[2.2.1]HEPTYL RING-SYSTEM [J].

BELKACEMI, D ;

DAVIES, JW ;

MALPASS, JR ;

NAYLOR, A ;

SMITH, CR .

TETRAHEDRON, 1992, 48 (46) :10161-10176

[4] RESTRICTED NITROGEN INVERSION IN N-METHYLPOLYHALOBENZ-7-AZANORBORNADIENES - H-1 DYNAMIC NMR-STUDIES AND MOLECULAR-CONFORMATION TRAPPING [J].

BUSHWELLER, CH ;

BROWN, JH ;

DIMEGLIO, CM ;

GRIBBLE, GW ;

EATON, JT ;

LEHOULLIER, CS ;

OLSON, ER .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (01) :268-271

[5] BRIDGED POLYCYCLIC COMPOUNDS .53. SOLVOLYSES OF EPIMERIC 7-CHLOROBENZONORBORNADIENES AND 5,12-DIPHENYL-6,11-DIHYDRO-6,11-(CHLOROMETHANO)-NAPHTHACENES [J].

CRISTOL, SJ ;

NACHTIGA.GW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (25) :7133-&

[6] NUCLEAR MAGNETIC RESONANCE SPECTRA OF PYRROLIZIDINE ALKALOIDS .2. PYRROLIZIDINE NUCLEUS IN ESTER AND NON-ESTER ALKALOIDS AND THEIR DERIVATIVES [J].

CULVENOR, CC ;

WOODS, WG .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1965, 18 (10) :1625-&

[7] NUCLEAR MAGNETIC RESONANCE SPECTRA OF PYRROLIZIDINE ALKALOIDS .1. SPECTRA OF RETRONECINE AND HELIOTRIDINE [J].

CULVENOR, CC ;

HEFFERNAN, ML ;

WOODS, WG .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1965, 18 (10) :1605-+

[8]

Davies A. R., UNPUB

[9] HETEROLYSIS OF N-CHLORO-1,2,3,4-TETRAHYDRO-1,4-IMINONAPHTHALENES AND RELATED SYSTEMS - EFFECTS OF STRUCTURE AND OF SOLVENT ON REACTION PATHWAYS [J].

DAVIES, JW ;

MALPASS, JR ;

MOSS, RE .

TETRAHEDRON LETTERS, 1986, 27 (34) :4071-4074

[10] ELECTRONIC CONTROL OF STEREOSELECTIVITY IN THE CHLORINATION OF 1,4-DIHYDRO-1,4-IMINONAPHTHALENES (7-AZABENZONORBORNADIENES) WITH N-CHLOROSUCCINIMIDE [J].

DAVIES, JW ;

DURRANT, ML ;

WALKER, MP ;

MALPASS, JR .

TETRAHEDRON, 1992, 48 (21) :4379-4398

← 1 2 3 →