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.
引用
收藏
页码:3915 / 3918
页数:4
相关论文
共 73 条
[1]  
AHLBRECHT H, 1976, SYNTHESIS-STUTTGART, P746
[2]  
AHLBRECHT H, 1982, SYNTHESIS-STUTTGART, P273
[3]  
AHLBRECHT H, 1980, SYNTHESIS-STUTTGART, P630
[4]   OPTIMIZATION AND APPLICATION OF LITHIUM PARAMETERS FOR PM3 [J].
ANDERS, E ;
KOCH, R ;
FREUNSCHT, P .
JOURNAL OF COMPUTATIONAL CHEMISTRY, 1993, 14 (11) :1301-1312
[5]   REACTIONS OF M(C5H4R)CL4 COMPLEXES (R=H, CH3) WITH PENTADIENYL ANIONS - PATHWAY VARIATIONS FOR NIOBIUM VS TANTALUM [J].
ARIF, AM ;
ERNST, RD ;
MELENDEZ, E ;
RHEINGOLD, AL ;
WALDMAN, TE .
ORGANOMETALLICS, 1995, 14 (04) :1761-1769
[6]   Alkali metal-1-azaallyl complexes: X-ray crystallographic, NMR spectroscopic and ab initio calculational studies [J].
Armstrong, DR ;
Clegg, W ;
Dunbar, L ;
Liddle, ST ;
MacGregor, M ;
Mulvey, RE ;
Reed, D ;
Quinn, SA .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1998, (20) :3431-3436
[7]   ADDITION OF ALKYLLITHIUM REAGENTS TO TRANS-CYCLOOCTENE - FACILE ELIMINATION OF LITHIUM HYDRIDE IN CYCLOOCTYL RING [J].
BACH, RD ;
BAIR, KW ;
WILLIS, CL .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1974, 77 (01) :31-37
[8]   Thermal cyclodimerization of aliphatic secondary C,N-dilithioallylamine derivatives [J].
Barluenga, J ;
Canteli, RM ;
Florez, J .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3753-3757
[9]   SILYLATION OF 2-AZA-1,3-DIENES - THE 1ST EXAMPLE OF A THERMALLY STABLE N-TRIMETHYL-SILYLDIVINYLAMINE [J].
BARLUENGA, J ;
JOGLAR, J ;
FUSTERO, S ;
GOTOR, V .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (04) :361-362
[10]   REACTIONS OF 1-AZA-PENTADIENYL ANIONS WITH MICHAEL ACCEPTORS - REGIOCHEMISTRY [J].
BAUMANN, F ;
WURTHWEIN, EU .
TETRAHEDRON LETTERS, 1991, 32 (36) :4683-4686