Substantial 2H-magnetic isotope effects on the diastereoselectivity of triplet photocycloaddition reactions

被引：13

作者：

Griesbeck, AG ^{[1
]}

Bondock, S ^{[1
]}

Cygon, P ^{[1
]}

机构：

[1] Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 30期

关键词：

D O I：

10.1021/ja0356232

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Magnetic isotope effects (MIE) on the diastereoselectivity of the triplet [2+2]-photocycloaddition of benzaldehyde with 2,3-dihydrofuran are described for four substrate combinations. The MIE results from H/D exchange at the reactive carbons of either the aldehyde or the alkene, respectively, but also from deuteration of the aromatic positions of benzaldehyde. Weaker isotope effects on the diastereoselectivity were detected for the reaction of α-deuterated propionaldehyde. Copyright © 2003 American Chemical Society.

引用

页码：9016 / 9017

页数：2

共 25 条

[1] Magnetic isotope effect: Nuclear spin control of chemical reactions [J].

Buchachenko, AL .

JOURNAL OF PHYSICAL CHEMISTRY A, 2001, 105 (44) :9995-10011

[2] Recent advances in spin chemistry [J].

Buchachenko, AL .

PURE AND APPLIED CHEMISTRY, 2000, 72 (12) :2243-2258

[3] MIE VERSUS CIE - COMPARATIVE-ANALYSIS OF MAGNETIC AND CLASSICAL ISOTOPE EFFECTS [J].

BUCHACHENKO, AL .

CHEMICAL REVIEWS, 1995, 95 (07) :2507-2528

[4]

Cai HL, 1997, TETRAHEDRON, V53, P10671

[5] SPIN-ORBIT-COUPLING IN BIRADICALS - ABINITIO MCSCF CALCULATIONS ON TRIMETHYLENE AND THE METHYL METHYL RADICAL PAIR [J].

CARLACCI, L ;

DOUBLEDAY, C ;

FURLANI, TR ;

KING, HF ;

MCIVER, JW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5323-5329

[6] DIASTEREOSELECTIVE NUCLEOPHILIC ADDITIONS TO IMINES ATTACHED TO TRICARBONYL(ARENE)CHROMIUM MOIETIES [J].

DAVID, DM ;

KANEMAGUIRE, LAP ;

PYNE, SG .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1994, (03) :289-295

[7] Secondary deuterium kinetic isotope effects in irreversible additions of allyl reagents to benzaldehyde [J].

Gajewski, JJ ;

Bocian, W ;

Brichford, NL ;

Henderson, JL .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (12) :4236-4240

[8] Spin-selectivity in photochemistry: A tool for organic synthesis [J].

Griesbeck, AG .

SYNLETT, 2003, (04) :451-472

[9]

Griesbeck AG, 2001, ANGEW CHEM INT EDIT, V40, P4684, DOI 10.1002/1521-3773(20011217)40:24<4684::AID-ANIE4684>3.0.CO

[10]

2-9

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