Influence of HMPA on reducing power and reactivity of SmBr2

被引:55
作者
Knettle, BW [1 ]
Flowers, RA [1 ]
机构
[1] Univ Toledo, Dept Chem, Toledo, OH 43606 USA
关键词
D O I
10.1021/ol0160957
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Addition of HMPA to SmBr2 in THF produces a reactant with an estimated redox potential of -2.63 +/- 0.01 V (vs AS/AgNO3), This powerful reductant is capable of reducing ketimines and alkyl chlorides at room temperature. Although the structure of the reductant has not been established, it is nonetheless a powerful addition to the arsenal of samarium based reductants currently utilized.
引用
收藏
页码:2321 / 2324
页数:4
相关论文
共 23 条
[1]   Samarium-induced iodine-catalyzed reduction of imines: synthesis of amine derivatives [J].
Banik, BK ;
Zegrocka, O ;
Banik, I ;
Hackfeld, L ;
Becker, FF .
TETRAHEDRON LETTERS, 1999, 40 (37) :6731-6734
[2]   CARBONYLATIONS MEDIATED BY DICYCLOPENTADIENYL SAMARIUM [J].
COLLIN, J ;
KAGAN, HB .
TETRAHEDRON LETTERS, 1988, 29 (47) :6097-6100
[3]  
CURRAN DP, 1992, SYNLETT, P943
[4]  
Enemærke RJ, 2000, CHEM-EUR J, V6, P3747, DOI 10.1002/1521-3765(20001016)6:20<3747::AID-CHEM3747>3.0.CO
[5]  
2-B
[6]   A ROUTE TO VICINAL DIAMINES FROM THE SAMARIUM(II) IODIDE-MEDIATED COUPLING OF ALDIMINES [J].
ENHOLM, EJ ;
FORBES, DC ;
HOLUB, DP .
SYNTHETIC COMMUNICATIONS, 1990, 20 (07) :981-987
[7]  
FLOWERS RA, UNPUB
[8]   The effect of lithium bromide and lithium chloride on the reactivity of SmI2 in THF [J].
Fuchs, JR ;
Mitchell, ML ;
Shabangi, M ;
Flowers, RA .
TETRAHEDRON LETTERS, 1997, 38 (47) :8157-8158
[9]   Samarium(II) triflate as a new reagent for the Grignard-type carbonyl addition reaction [J].
Fukuzawa, S ;
Mutoh, K ;
Tsuchimoto, T ;
Hiyama, T .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5400-5405
[10]  
HARRIS DC, 1978, SYMMETRY SPECTROSCOP, P397