Efficient one-pot synthesis of secondary cyclic phosphanes with easy regeneration of the phosphorus-donor reagent used

被引:14
作者
Baccolini, G [1 ]
Boga, C [1 ]
Galeotti, M [1 ]
机构
[1] Univ Bologna, Dipartimento Chim Organ, I-40136 Bologna, Italy
关键词
hypervalent compounds; phosphanes; phosphorus heterocycles; synthetic methods;
D O I
10.1002/anie.200453820
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Phosphanes: No pain, all gain. A regenerable phosphorus donor is the key to an efficient and economic one-pot synthesis of five- and six-membered secondary cyclic phosphanes. The reaction, at room temperature, of 1 with 1 equivalent of bis(Grignard reagent) 2 followed by treatment with aqueous acid gives cyclic phosphanes 3 in 70-80% yield and the new compound 4. Simply treating 4 with PCl3 quantitatively regenerates the starting reagent 1, which can be reused without further purification.
引用
收藏
页码:3058 / 3060
页数:3
相关论文
共 28 条
[1]   Flash vacuum pyrolysis of dichlorophosphines over magnesium: Generation and reactivity of simple phosphinidenes [J].
Aitken, RA ;
Masamba, W ;
Wilson, NJ .
TETRAHEDRON LETTERS, 1997, 38 (48) :8417-8420
[2]  
Baccolini G, 1997, HETEROATOM CHEM, V8, P551, DOI 10.1002/(SICI)1098-1071(1997)8:6<551::AID-HC15>3.0.CO
[3]  
2-Q
[4]   BENZOTHIADIPHOSPHOLE AS PHOSPHORUS DONATING REAGENT FOR A NEW ROUTE TO 2H-1,2,3-DIAZAPHOSPHOLE DERIVATIVES [J].
BACCOLINI, G ;
ORSOLAN, G ;
MEZZINA, E .
TETRAHEDRON LETTERS, 1995, 36 (03) :447-450
[5]  
Baccolini G, 2000, SYNLETT, P1685
[6]   FACILE SYNTHESIS OF FUSED BENZO-1,2,3-THIADIPHOSPHOLES, A NEW HETEROCYCLIC SYSTEM [J].
BACCOLINI, G ;
MEZZINA, E ;
TODESCO, PE ;
FORESTI, E .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (04) :304-305
[7]   Silylphosphide reagents in synthetic routes to cyclophosphines [J].
Brandt, PF ;
Schubert, DM ;
Norman, AD .
INORGANIC CHEMISTRY, 1997, 36 (08) :1728-1731
[8]   CHEMISTRY OF THE C4H8P RING - THE AMINOPHOSPHINE (CH3)2NPC4H8, THE CYCLOPHOSPHINE C4H8PH AND THE TETRACYCLIC TRIMER (C4H8PBH2)3 [J].
BURG, AB ;
SLOTA, PJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (09) :2148-2151
[9]   ASYMMETRIC CATALYTIC SYNTHESIS OF BETA-BRANCHED AMINO-ACIDS VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS [J].
BURK, MJ ;
GROSS, MF ;
MARTINEZ, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (36) :9375-9376
[10]   Bis(phospholane) ligands containing chiral backbones.: Matching and mismatching effects in enantioselective hydrogenation of α-keto esters [J].
Burk, MJ ;
Pizzano, A ;
Martín, JA ;
Liable-Sands, LM ;
Rheingold, AL .
ORGANOMETALLICS, 2000, 19 (03) :250-260