ZIRCONIUM-PROMOTED INTRAMOLECULAR CYCLIZATION OF TERMINAL ALKYNES AND UNUSUAL CARBONYLATION REACTION

被引:21
作者
BARLUENGA, J
SANZ, R
FANANAS, FJ
机构
关键词
D O I
10.1039/c39950001009
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
N-(2-bromoallyl)-N-prop-2-ynyl- and N-allyl-N-(2-bromoallyl)-amines 1 and 5 undergo intramolecular cyclization by using zirconocene methyl chloride to give zirconacycles 4 and 6, respectively, which are characterized by deuteriolysis affording products 2 and 7; carbonylation of 6 and further reaction with electrophiles (deuterium oxide, allyl bromide, 4-chlorobenzonitrile, benzaldehyde, benzophenone and benzylideneaniline) leads to compounds 8, 9 and 11-15.
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页码:1009 / 1010
页数:2
相关论文
共 20 条
[1]   REGIOSELECTIVE ZIRCONIUM-MEDIATED CROSS-COUPLING OF N-METHYL-N-PROPARGYL ANILINE AND ALKENES [J].
BARLUENGA, J ;
SANZ, R ;
FANANAS, FJ .
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1995, 50 (03) :312-314
[2]   N-SUBSTITUTED LITHIUM 2-LITHIOALLYLAMINES - NEW INTERMEDIATES IN SYNTHESIS [J].
BARLUENGA, J ;
FOUBELO, F ;
FANANAS, FJ ;
YUS, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (03) :553-557
[3]   ALLYLAMINE FUNCTIONALIZATION THROUGH BETA-NITROGEN-FUNCTIONALIZED ORGANOLITHIUM COMPOUNDS [J].
BARLUENGA, J ;
CANTELI, RM ;
FLOREZ, J .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (06) :1586-1588
[4]   PREPARATION AND REACTIVITY OF NEW BETA-NITROGEN-FUNCTIONALIZED VINYLIC ORGANOLITHIUM COMPOUNDS FROM SECONDARY ALIPHATIC ALLYLAMINES [J].
BARLUENGA, J ;
CANTELI, RM ;
FLOREZ, J .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (03) :602-606
[5]   ZIRCONOCENE COMPLEXES OF UNSATURATED ORGANIC-MOLECULES - NEW VEHICLES FOR ORGANIC-SYNTHESIS [J].
BROENE, RD ;
BUCHWALD, SL .
SCIENCE, 1993, 261 (5129) :1696-1701
[6]   GROUP-4 METAL-COMPLEXES OF BENZYNES, CYCLOALKYNES, ACYCLIC ALKYNES, AND ALKENES [J].
BUCHWALD, SL ;
NIELSEN, RB .
CHEMICAL REVIEWS, 1988, 88 (07) :1047-1058
[7]   STRUCTURE-REACTIVITY CORRELATIONS FOR THE FORMATION OF ZIRCONOCENE ETA-2-IMINE COMPLEXES FROM AMINES [J].
COLES, N ;
HARRIS, MCJ ;
WHITBY, RJ ;
BLAGG, J .
ORGANOMETALLICS, 1994, 13 (01) :190-199
[8]   SYNTHESIS OF RACEMIC ALPHA-TRANS-BERGAMOTENE AND BETA-TRANS-BERGAMOTENE [J].
COREY, EJ ;
CANE, DE ;
LIBIT, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (25) :7016-&
[9]   DIMERIC (ETA-2-BENZOPHENONE)ZIRCONOCENE - ITS REMARKABLE STRUCTURE AND CHEMISTRY [J].
ERKER, G ;
DORF, U ;
CZISCH, P ;
PETERSEN, JL .
ORGANOMETALLICS, 1986, 5 (04) :668-676
[10]   NOVEL SYNTHESIS OF NITROGEN-HETEROCYCLES USING ZIRCONIUM-PROMOTED REDUCTIVE COUPLING - FORMAL TOTAL SYNTHESIS OF DENDROBINE [J].
MORI, M ;
UESAKA, N ;
SHIBASAKI, M .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (13) :3519-3521