Copper(I)-catalyzed intramolecular photocycloadditions of dicyclopentadiene derivatives linked by removable tethers

被引：11

作者：

Chebolu, R

Zhang, W

Galoppini, E

Gilardi, R

机构：

[1] Rutgers State Univ, Dept Chem, Newark, NJ 07102 USA

[2] USN, Res Lab, Struct Matter Lab, Washington, DC 20375 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 16期

关键词：

intramolecular photocycloaddition; copper catalyzed; dicyclopentadiene; polycyclic compounds;

D O I：

10.1016/S0040-4039(00)00273-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cu(I)-catalyzed intramolecular [2+2] photocycloadditions of two dicyclopentadiene derivatives linked by an alkyl chain have been studied. These reactions are regio- and stereoselective and proceed considerably faster than the corresponding intermolecular reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.

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页码：2831 / 2834

页数：4

相关论文

共 10 条

[1] STEREOCHEMISTRY OF PENTACYCLO[8.2.1.14,7.O2,9.O3,8]TETRADECANES AND -DIENES . NORBORNENE AND NORBORNADIENE DIMERS [J].

ARNOLD, DR ;

TRECKER, DJ ;

WHIPPLE, EB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (12) :2596-&

[2] PREPARATION AND PROPERTIES OF CAGE POLYCYCLIC SYSTEMS .1. PENTACYCLO(5.3.0.02,5.03,9.04,8!DECANE AND PENTACYCLO 4.3.0.02,5.03,8.04,7!NONANE DERIVATIVES [J].

CHAPMAN, NB ;

KEY, JM ;

TOYNE, KJ .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (11) :3860-&

[3] MOLYBDENUM-MEDIATED DIMERIZATION OF NORBORNADIENE AND DERIVATIVES [J].

CHOW, TJ ;

CHAO, YS ;

LIU, LK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (03) :797-804

[4] Intramolecular photocycloaddition of a tethered bis-2,3-dihydro-4-pyridone: Stereochemistry and reactivity of the cycloadduct [J].

Comins, DL ;

Lee, YS ;

Boyle, PD .

TETRAHEDRON LETTERS, 1998, 39 (3-4) :187-190

[5] CYCLOADDITIONS .30. COPPER(I)-CATALYZED INTRAMOLECULAR DIENE-DIENE CYCLOADDITION REACTIONS AND REARRANGEMENTS [J].

HERTEL, R ;

MATTAY, J ;

RUNSINK, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :657-665

[6]

LANGER K, 1995, CRC HDB ORGANIC PHOT, P84

[7] STEREOCHEMISTRY OF THE REACTION OF 7-SUBSTITUTED NORBORNADIENES WITH IRON CARBONYLS .3. REACTION OF FE(CO)5 WITH 7-(BENZOYLOXY)NORBORNADIENE [J].

MARCHAND, AP ;

EARLYWINE, AD ;

HEEG, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (22) :4096-4100

[8] HOMOGENEOUS METAL-CATALYSIS IN ORGANIC-PHOTOCHEMISTRY [J].

SALOMON, RG .

TETRAHEDRON, 1983, 39 (04) :485-575

[9] COPPER(I) CATALYSIS IN PHOTOCYCLOADDITIONS .1. NORBORNENE [J].

SALOMON, RG ;

KOCHI, JK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (04) :1137-1144

[10] THE MECHANISM OF THE DIELS-ALDER REACTION [J].

WOODWARD, RB ;

KATZ, TJ .

TETRAHEDRON, 1959, 5 (01) :70-89