REARRANGEMENT OF ORTHO-ALKYNYL SUBSTITUTED ALPHA-DIAZOACETOPHENONES - CONVERSION TO BETA-NAPHTHOLS VIA ARYLKETENE INTERMEDIATES

被引：42

作者：

PADWA, A

AUSTIN, DJ

CHIACCHIO, U

KASSIR, JM

RESCIFINA, A

XU, SL

机构：

[1] Department of Chemistry, Emory University Atlanta

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 42期

关键词：

D O I：

10.1016/S0040-4039(00)79427-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In contrast to the rhodium (II) mediated cycloisomerization of o-alkynyl substituted alpha-diazoacetophenones, irradiation leads to beta-naphthols which are formed via cyclization of an arylketene intermediate.

引用

页码：5923 / 5926

页数：4

共 28 条

[1] TRANSITION-METAL-CATALYZED REACTIONS OF DIAZO-COMPOUNDS .1. CYCLOPROPANATION OF DOUBLE-BONDS [J].

ANCIAUX, AJ ;

HUBERT, AJ ;

NOELS, AF ;

PETINIOT, N ;

TEYSSIE, P .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (04) :695-702

[2]

Ando W., 1978, CHEM DIAZONIUM DIA 1, P458

[3]

Burke S. D., 1979, ORG REACTIONS, V26, P361, DOI DOI 10.1002/0471264180.0R026.02

[4] ALKYNYLCYANOKETENES - UNUSUAL REARRANGEMENTS ARISING FROM THE REACTIONS OF ALKYNYLCYANOKETENES WITH ALKYNES [J].

CHOW, K ;

NGUYEN, NV ;

MOORE, HW .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (12) :3876-3880

[5] AN ANNULATION METHOD FOR THE SYNTHESIS OF HIGHLY SUBSTITUTED POLYCYCLIC AROMATIC AND HETEROAROMATIC-COMPOUNDS [J].

DANHEISER, RL ;

BRISBOIS, RG ;

KOWALCZYK, JJ ;

MILLER, RF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (08) :3093-3100

[6] TOTAL SYNTHESIS OF MYCOPHENOLIC-ACID [J].

DANHEISER, RL ;

GEE, SK ;

PEREZ, JJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (04) :806-810

[7]

DANHEISER RL, 1984, J ORG CHEM, V49, P12672

[8]

DAVE D, 1970, ORG REACTIONS, V18, P217

[9] CATALYTIC METHODS FOR METAL CARBENE TRANSFORMATIONS [J].

DOYLE, MP .

CHEMICAL REVIEWS, 1986, 86 (05) :919-939

[10] ELECTROPHILIC METAL CARBENES AS REACTION INTERMEDIATES IN CATALYTIC REACTIONS [J].

DOYLE, MP .

ACCOUNTS OF CHEMICAL RESEARCH, 1986, 19 (11) :348-356

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