A new rearrangement of cyclic allenes via 1,2-dehydro[10]annulenes:: formation of benzo[c]fluorenones

被引:28
作者
Rodríguez, D [1 ]
Navarro-Vázquez, A [1 ]
Castedo, L [1 ]
Domínguez, D [1 ]
Saá, C [1 ]
机构
[1] Univ Santiago de Compostela, Fac Quim, CSIC, Dept Quim Organ & Unidad Asociada, Santiago De Compostela 15782, Spain
关键词
dehydro Diels-Alder reaction; cyclic allenes; 1,2-dehydro[10]annulenes; benzo[b]fluorenones; benzo[c]fluorenones;
D O I
10.1016/S0040-4039(02)00368-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new rearrangement of cyclic allenes giving benzo[C]fluorenones was observed when studying intramolecular dehydro Diels-Alder reactions of siyl-substituted alkynes with arenynes (aryldiacetylenes). (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2717 / 2720
页数:4
相关论文
共 12 条
[1]   Formation of benzo[b]fluorenes and the benzo[a]fluorene core of the fluostatins by cyclization of diaryldiynones [J].
Atienza, C ;
Mateo, C ;
de Frutos, O ;
Echavarren, AM .
ORGANIC LETTERS, 2001, 3 (02) :153-155
[2]   Generation, characterization, and rearrangements of 4,5-benzocyclohepta-1,2,4,6-tetraene [J].
Bonvallet, PA ;
McMahon, RJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (38) :9332-9333
[3]   Strained cyclic cumulene intermediates in Diels-Alder cycloadditions of enynes and diynes [J].
Burrell, RC ;
Daoust, KJ ;
Bradley, AZ ;
DiRico, KJ ;
Johnson, RP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (17) :4218-4219
[4]   INTRAMOLECULAR [4+2] CYCLOADDITION REACTIONS OF CONJUGATED ENYNES [J].
DANHEISER, RL ;
GOULD, AE ;
DELAPRADILLA, RF ;
HELGASON, AL .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) :5514-5515
[5]   Steric hindrance facilitated synthesis of enynes and their intramolecular [4+2] cycloaddition with alkynes [J].
González, JJ ;
Francesch, A ;
Cárdenas, DJ ;
Echavarren, AM .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) :2854-2857
[6]   7H-benzo[c]fluorene:: a major DNA adduct-forming component of coal tar [J].
Koganti, A ;
Singh, R ;
Rozett, K ;
Modi, N ;
Goldstein, LS ;
Roy, TA ;
Zhang, FJ ;
Harvey, RG ;
Weyand, EH .
CARCINOGENESIS, 2000, 21 (08) :1601-1609
[7]   Strained intermediates in intramolecular dehydro Diels-Alder reactions:: Rearrangement of cyclic allenes via 1,2-dehydro[10]annulenes [J].
Rodríguez, D ;
Navarro-Vázquez, A ;
Castedo, L ;
Domínguez, D ;
Saá, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (37) :9178-9179
[8]   Synthesis of the benzo[b]fluorene core of the kinamycins by cycloaromatization of non-conjugated benzotriynes [J].
Rodríguez, D ;
Castedo, L ;
Domínguez, D ;
Saá, C .
TETRAHEDRON LETTERS, 1999, 40 (43) :7701-7704
[9]   Intramolecular [4+2] cycloaddition reactions of diarylacetylenes:: Synthesis of benzo[b]fluorene derivatives via cyclic allenes [J].
Rodríguez, D ;
Navarro, A ;
Castedo, L ;
Domínguez, D ;
Saá, C .
ORGANIC LETTERS, 2000, 2 (11) :1497-1500
[10]   Benzo[b]fluorenes formed in the thermal cyclization of 3-ene-1,6-diynes [J].
Schmittel, M ;
Strittmatter, M ;
Schenk, WA ;
Hagel, M .
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1998, 53 (09) :1015-1020