Reaction behavior of cumulene in Diels-Alder and Friedel-Crafts reactions

被引：14

作者：

Asakawa, Tomohiro ^{[1
]}

Iinuma, Mie ^{[1
]}

Furuta, Takumi ^{[1
]}

Fujii, Satoshi ^{[1
]}

Kan, Toshiyuki ^{[1
]}

Tanaka, Kiyoshi ^{[1
]}

机构：

[1] Univ Shizuoka, Sch Pharmaceut Sci, Suruga Ku, Shizuoka 4228526, Japan

来源：

CHEMISTRY LETTERS | 2006年 / 35卷 / 05期

关键词：

D O I：

10.1246/cl.2006.512

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Diels-Alder and Friedel-Crafts reactions of [3]cumulene 1 were investigated. Although the Diels-Alder reaction with cyclopentadiene selectively occurred on the C2, 3 double bond to give tetrasubstituted allenyl products, the Friedel-Crafts addition of electron-rich heteroaromatics and subsequent protonation cleanly occurred on the C3, 4 double bond to afford tetrasubstituted conjugated dienes.

引用

页码：512 / 513

页数：2

共 16 条

[1] Synthesis of trisubstituted furans from epoxypropargyl esters by sequential SmI2-promoted reduction-elimination and Pd(II)-catalyzed cycloisomerization [J].

Aurrecoechea, JM ;

Pérez, E ;

Solay, M .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (02) :564-569

[2] CYCLOPROPANONES FROM THE OXIDATION OF HINDERED [4]-CUMULENES AND [5]-CUMULENES WITH EPOXIDATION REAGENTS [J].

CRANDALL, JK ;

COPPERT, DM ;

SCHUSTER, T ;

LIN, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (15) :5998-6002

[3]

GARCIA JG, 1995, TETRAHEDRON LETT, V36, P7391

[4] Concerning cumulene I. Syntheses of tetraphenyl-hexapentaen and di-biphenylene-hexapentaen. [J].

Kuhn, R ;

Wallenfels, K .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1938, 71 :783-790

[5] UBER KUMULENE-IV - OKTAHEPTAENE [J].

KUHN, R ;

ZAHN, H .

CHEMISCHE BERICHTE-RECUEIL, 1951, 84 (5-6) :566-570

[6] Selective oestrogen receptor modulation: Molecular pharmacology for the millennium [J].

Levenson, AS ;

Jordan, VC .

EUROPEAN JOURNAL OF CANCER, 1999, 35 (12) :1628-1639

[7] Tetrabromobutatriene: Completing the perhalocumulene series [J].

Liu, PH ;

Li, L ;

Webb, JA ;

Zhang, Y ;

Goroff, NS .

ORGANIC LETTERS, 2004, 6 (13) :2081-2083

[8] A REACTION CASCADE LEADING TO 1,6-DIDEHYDRO[10]ANNULENE -] 1,5-DEHYDRONAPHTHALENE CYCLIZATION INITIATED BY THIOL ADDITION [J].

MYERS, AG ;

DRAGOVICH, PS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :7021-7022

[9] A novel attractive interaction in the Diels-Alder reaction of N-protected pyrroles with allene-1,3-dicarboxylates [J].

Nishide, K ;

Ichihashi, S ;

Kimura, H ;

Katoh, T ;

Node, N .

TETRAHEDRON LETTERS, 2001, 42 (52) :9237-9240

[10] REACTIONS OF POLY(ORGANYLTHIO)BUTENYNES AND POLY(ORGANYLTHIO)BUTATRIENES WITH ELECTROPHILIC REAGENTS [J].

ROEDIG, A ;

ZABY, G .

CHEMISCHE BERICHTE-RECUEIL, 1980, 113 (10) :3342-3351

← 1 2 →