Generation of 1-azapentadienyl anion from N-(tert-butyldimethylsilyl)-3-buten-1-amine

被引:12
作者
Jacobson, MA [1 ]
Williard, PG [1 ]
机构
[1] Brown Univ, Dept Chem, Providence, RI 02912 USA
关键词
D O I
10.1021/jo0162336
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-(tert-Butyldimethylsilyl)-3-buten-1-amine undergoes allylic deprotonation at the 2-position when exposed to 2 equiv of nBuLi in THE This allylic anion undergoes lithium hydride elimination to generate a 1-azapentadienyl anion. The anion is generated cleanly and completely.
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收藏
页码:3915 / 3918
页数:4
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共 73 条
[21]   THE PREPARATION OF THE 2,4-DI(TERT-BUTYL)PENTADIENYL ANION AND ITS TI(II), CR(II), AND ZN(II) COMPLEXES [J].
ERNST, RD ;
FREEMAN, JW ;
SWEPSTON, PN ;
WILSON, DR .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 402 (01) :17-25
[22]   Reorientation dynamics within ion-paired allylic lithium compounds: Isolation of inversion processes [J].
Fraenkel, G ;
Cabral, J ;
Lanter, C ;
Wang, JH .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) :1302-1310
[23]   Restricted stereochemistry of solvation of allylic lithium compounds: Structural and dynamic consequences [J].
Fraenkel, G ;
Duncan, JH ;
Wang, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (02) :432-443
[24]   SYNTHESES, CHARACTERIZATION, AND STRUCTURAL STUDIES OF LEWIS BASE ADDUCTS OF HALF-OPEN VANADOCENES, V(C5H5)(PDL)(L) [J].
GEDRIDGE, RW ;
HUTCHINSON, JP ;
RHEINGOLD, AL ;
ERNST, RD .
ORGANOMETALLICS, 1993, 12 (05) :1553-1558
[25]   Reactions of enimines with [Cp*RuCl]4:: Half-open ruthenocene and related species incorporating heteroatoms [J].
Gutierrez, JA ;
Clemente, MEN ;
Paz-Sandoval, MA ;
Arif, AM ;
Ernst, RD .
ORGANOMETALLICS, 1999, 18 (06) :1068-1079
[26]   Synthesis, characterization and a theoretical investigation of the formation of silicon, germanium and tin azapentadiene compounds from lithium azapentadienyls [J].
Gutiérrez, JA ;
Paz-Sandoval, MA ;
Robles, J .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 599 (02) :147-158
[27]   PENTADIENYL AS A STRONGER BINDING BUT MORE REACTIVE LIGAND THAN CYCLOPENTADIENYL - SYNTHESES, REACTIONS, AND MOLECULAR-ORBITAL STUDIES OF HALF-OPEN TITANOCENES [J].
HYLAKRYSPIN, I ;
WALDMAN, TE ;
MELENDEZ, E ;
TRAKARNPRUK, W ;
ARIF, AM ;
ZIEGLER, ML ;
ERNST, RD ;
GLEITER, R .
ORGANOMETALLICS, 1995, 14 (11) :5030-5040
[28]   Synthesis of 2,3-disubstituted pyrroles from 3,N-dilithio-N-(tert-butyldimethylsilyl)-2-buten-1-amine [J].
Jacobson, MA ;
Williard, PG .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) :32-37
[29]  
KIECZYKOWSKI GR, 1976, TETRAHEDRON LETT, P597
[30]   Structure and chemical behavior of an eta(5)-(1-azapentadienyl)lithium derivative generated by deprotonation reactions starting from 9-(N-tert-butylaminomethyl)fluorene or 6-(tert-butylamino)dibenzofulvene [J].
Konemann, M ;
Erker, G ;
Frohlich, R ;
Wurthwein, EU .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (46) :11155-11164