Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes.: Part 14:: Regioselectivity of the opening reactions with MeOH of remote O-substituted 1,2-epoxycyclohexanes under gas-phase operating conditions

被引：20

作者：

Crotti, P

Di Bussolo, V

Favero, L

Pineschi, M

Marianucci, F

Renzi, G

Amici, G

Roselli, G

机构：

[1] Univ Pisa, Dipartimento Chim Bioorgan & Biofarm, I-56126 Pisa, Italy

[2] Univ Camerino, Dipartimento Sci Chim, I-62032 Camerino, Italy

来源：

TETRAHEDRON | 2000年 / 56卷 / 38期

关键词：

epoxides; regioselection; gas phase reactions; chelation;

D O I：

10.1016/S0040-4020(00)00643-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The regiochemical behavior of cyclohexene oxides bearing a remote O-functionality was determined in the gas-phase in opening reactions with MeOH, using a gaseous acid (D-3(+), CnH5+, Me2F+) as the promoting agent. The results obtained indicate the incursion in the opening process in the gas phase of H+ (or D+)-mediated chelated bidentate species completely absent in the corresponding reactions (methanolysis) carried out in the condensed phase. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：7513 / 7524

页数：12

相关论文

共 23 条

[1] EFFECT OF ADDITIVES ON IONIC REACTION MECHANISM IN RADIOLYSIS OF METHANE [J].

AUSLOOS, P ;

LIAS, SG ;

GORDEN, R .

JOURNAL OF CHEMICAL PHYSICS, 1963, 39 (12) :3341-&

[2] GAS-PHASE RADIOLYSIS OF PROPANE [J].

AUSLOOS, P ;

LIAS, S .

JOURNAL OF CHEMICAL PHYSICS, 1962, 36 (12) :3163-&

[3]

AUSLOOS P, 1970, ION MOL REACTIONS

[4] REGIOCHEMICAL CONTROL OF THE RING-OPENING OF 1,2-EPOXIDES BY MEANS OF CHELATING PROCESSES .8. SYNTHESIS AND RING-OPENING REACTIONS OF CIS-OXIDES AND TRANS-OXIDES DERIVED FROM 3-BENZYLOXYCYCLOHEXENE AND 2-BENZYLOXY-5,6-DIHYDRO-2H-PYRAN [J].

CALVANI, F ;

CROTTI, P ;

GARDELLI, C ;

PINESCHI, M .

TETRAHEDRON, 1994, 50 (45) :12999-13022

[5] AROMATIC SUBSTITUENT EFFECT ON THE STEREOSELECTIVITY OF THE GAS-PHASE ACID-INDUCED RING-OPENING IN 9,10-OXIDES DERIVED FROM TRANS-1,2,3,4,4A,10A-HEXAHYDROPHENANTHRENE [J].

CHINI, M ;

CROTTI, P ;

MINUTOLO, F ;

DEZI, E ;

LOMBARDOZZI, A ;

PIZZABIOCCA, A ;

RENZI, G .

TETRAHEDRON, 1993, 49 (26) :5845-5858

[6] REGIOCHEMICAL CONTROL OF THE RING-OPENING OF 1,2-EPOXIDES BY MEANS OF CHELATING PROCESSES .2. SYNTHESIS AND REACTIONS OF THE CIS-OXIDE AND TRANS-OXIDE OF 4-[(BENZYLOXY)METHYL]CYCLOHEXENE, 3-CYCLOHEXENEMETHANOL, AND METHYL 3-CYCLOHEXENECARBOXYLATE [J].

CHINI, M ;

CROTTI, P ;

FLIPPIN, LA ;

MACCHIA, F ;

PINESCHI, M .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) :1405-1412

[7] REGIOCHEMICAL CONTROL OF THE RING-OPENING OF 1,2-EPOXIDES BY MEANS OF CHELATING PROCESSES - SYNTHESIS AND REACTIONS OF THE CIS-OXIDES AND TRANS-OXIDES DERIVED FROM 4-(BENZYLOXY)CYCLOHEXENE [J].

CHINI, M ;

CROTTI, P ;

FLIPPIN, LA ;

MACCHIA, F .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (14) :4265-4272

[8] REGIOCHEMICAL CONTROL OF THE RING-OPENING OF 1,2-EPOXIDES BY MEANS OF CHELATING PROCESSES .4. SYNTHESIS AND REACTIONS OF THE CIS-OXIDES AND TRANS-OXIDES DERIVED FROM 3-[(BENZYLOXY)METHYL]CYCLOHEXENE [J].

CHINI, M ;

CROTTI, P ;

FLIPPIN, LA ;

GARDELLI, C ;

MACCHIA, F .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1713-1718

[9] REGIOCHEMICAL CONTROL OF THE RING-OPENING OF 1,2-EPOXIDES BY MEANS OF CHELATING PROCESSES .3. AMINOLYSIS AND AZIDOLYSIS OF THE CIS-OXIDES AND TRANS-OXIDES DERIVED FROM 4-(BENZYLOXY)CYCLOHEXENE [J].

CHINI, M ;

CROTTI, P ;

FLIPPIN, LA ;

MACCHIA, F .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (25) :7043-7048

[10] Aromatic substituent effect on the stereoselectivity of the condensed- and gas-phase acid-induced methanolysis in 2-aryloxiranes derived from 3,4-dihydronaphthalene and trans-1,2,3,4,4a,10a-hexahydrophenanthrene bearing a tertiary benzylic oxirane nucleophilic centre [J].

Crotti, P ;

DiBussolo, V ;

Favero, L ;

Pineschi, M ;

Sergiampietri, D ;

Renzi, G ;

Ricciutelli, M ;

Roselli, G .

TETRAHEDRON, 1997, 53 (15) :5515-5536