The regiochemistry of intramolecular photochemical [2+2] cycloaddition reactions: Biradical conformation control.

被引：8

作者：

Audley, M ^{[1
]}

Geraghty, NWA ^{[1
]}

机构：

[1] NATL UNIV IRELAND UNIV COLL GALWAY,DEPT CHEM,GALWAY,IRELAND

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 10期

关键词：

D O I：

10.1016/0040-4039(96)00080-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A basic MM2 force-field is shown to give minimum energy conformations for radicals which are generally comparable to those obtained previously using a modified force-field. The conformations of biradicals determined by the method are used to assess whether this factor plays a role in determining the regiochemistry of photochemical [2+2] cycloaddition reactions. This concept of biradical conformation control is shown to account for behaviour which is difficult to rationalise using the 'rule of five'.

引用

页码：1641 / 1644

页数：4

共 20 条

[11] PHOTOSENSITIZED INTERNAL ADDITION OF DIENES TO OLEFINS [J].

LIU, RSH ;

HAMMOND, GS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (19) :4936-&

[12] MECHANISM OF ENONE PHOTOANNELATION - ACTIVATION-ENERGIES AND ROLE OF EXCIPLEXES [J].

LOUTFY, RO ;

DEMAYO, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (11) :3559-3565

[13] REGIOCHEMICAL CONTROL IN INTRAMOLECULAR PHOTOCHEMICAL-REACTIONS OF 1,6-HEPTADIENES - CARBONYL-SUBSTITUTED 1-(4-ALKENYL)-1-CYCLOPENTENES [J].

MATLIN, AR ;

GEORGE, CF ;

WOLFF, S ;

AGOSTA, WC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (12) :3385-3394

[14]

MCARDLE P, 1994, J APPL CRYSTALLOGR, V27, P438

[15]

MONAGHAN MJ, UNPUB

[16] DEAZETATION OF A BICYCLIC AZO COMPOUND - RESOLUTION OF A STEREOCHEMICAL AMBIGUITY AND CONFORMATIONAL-ANALYSIS OF A BIRADICAL [J].

SAMUEL, CJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (07) :1259-1265

[17] ARE TRIPLET EXCIPLEXES INVOLVED IN [2+2] PHOTOCYCLOADDITION OF CYCLIC ENONES TO ALKENES [J].

SCHUSTER, DI ;

HEIBEL, GE ;

BROWN, PB ;

TURRO, NJ ;

KUMAR, CV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (24) :8261-8263

[18] NEW INSIGHTS INTO AN OLD MECHANISM - [2 + 2] PHOTOCYCLOADDITION OF ENONES TO ALKENES [J].

SCHUSTER, DI ;

LEM, G ;

KAPRINIDIS, NA .

CHEMICAL REVIEWS, 1993, 93 (01) :3-22

[19] MERCURY (3P1) PHOTOSENSITIZED INTERNAL CYCLOADDITION REACTIONS IN 1,4-, 1,5-, AND 1,6-DIENES [J].

SRINIVAS.R ;

CARLOUGH, KH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (19) :4932-&

[20] A SHORT SYNTHESIS OF TRICYCLO[4.2.0.01,4]OCTANES [J].

WOLFF, S ;

AGOSTA, WC .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (24) :4821-4825

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