A novel scandium ortho-methoxynitrosobenzene-dimer complex: mechanistic implications for the nitroso-Diels-Alder reaction

被引：34

作者：

Lightfoot, AP

Pritchard, RG

Wan, H

Warren, JE

Whiting, A

机构：

[1] Univ Durham, Dept Chem, Univ Sci Labs, Durham DH1 3LE, England

[2] GlaxoSmithKline Pharmaceut, Harlow CM19 5AW, Essex, England

[3] UMIST, Dept Chem, Manchester M60 1QD, Lancs, England

来源：

CHEMICAL COMMUNICATIONS | 2002年 / 18期

关键词：

D O I：

10.1039/b206366b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Arylnitroso dienophiles exist in equilibrium with their dimeric counterparts, which in turn form stable bidentate complexes with scandium(III) triflate and react with cyclohexadiene to give the corresponding Diels-Alder adduct at the same rate as the normal thermal process.

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页码：2072 / 2073

页数：2

相关论文

共 22 条

[1] Total synthesis of (-)-epibatidine using an asymmetric Diels-Alder reaction with a chiral N-acylnitroso dienophile [J].

Aoyagi, S ;

Tanaka, R ;

Naruse, M ;

Kibayashi, C .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8397-8406

[2]

Boger D. L., 1987, HETERO DIELS ALDER M

[3] ASYMMETRIC DIELS-ALDER CYCLOADDITIONS WITH CHIRAL CARBAMOYL DIENOPHILES [J].

DEFOIN, A ;

BROUILLARDPOICHET, A ;

STREITH, J .

HELVETICA CHIMICA ACTA, 1992, 75 (01) :109-123

[4] Structural investigations of C-nitrosobenzenes. Part 2. NMR studies of monomer-dimer equilibria including restricted nitroso group rotation in monomers [J].

Fletcher, DA ;

Gowenlock, BG ;

Orrell, KG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1998, (04) :797-803

[5] Structural investigations of C-nitrosobenzenes .1. Solution state H-1 NMR studies [J].

Fletcher, DA ;

Gowenlock, BG ;

Orrell, KG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1997, (11) :2201-2205

[6] 4-iodonitrosobenzene. Structural and spectroscopic studies of the monomeric solid and of previously unreported dimers [J].

Fletcher, DA ;

Gowenlock, BG ;

Orrell, KG ;

Sik, V ;

Hibbs, DE ;

Hursthouse, MB ;

Malik, KMA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1996, (02) :191-197

[7] Direct evidence for a ruthenium(IV) oxo complex-mediated oxidation of a hydroxamic acid in the presence of phosphine oxide donors [J].

Flower, KR ;

Lightfoot, AP ;

Wan, HL ;

Whiting, A .

CHEMICAL COMMUNICATIONS, 2001, (18) :1812-1813

[8]

Gowenlock BG, 2001, J CHEM SOC PERK T 2, P1904

[9] ASYMMETRIC INDUCTION IN THE DIELS-ALDER REACTIONS OF ALPHA-HYDROXYACYLNITROSO COMPOUNDS [J].

KIRBY, GW ;

NAZEER, M .

TETRAHEDRON LETTERS, 1988, 29 (47) :6173-6174

[10]

Liang JL, 2001, CHEM-EUR J, V7, P2306, DOI 10.1002/1521-3765(20010601)7:11<2306::AID-CHEM23060>3.0.CO