ORGANIC SYNTHESES WITH TRANSITION-METAL COMPLEXES .52. N-VINYLAMINOCARBENE AND N-(2-PROPENYL)AMINOCARBENE COMPLEXES BY ADDITION OF KETENE IMINES TO CARBENE IRON COMPLEXES

被引:7
作者
AUMANN, R [1 ]
TRENTMANN, B [1 ]
DARTMANN, M [1 ]
KREBS, B [1 ]
机构
[1] UNIV MUNSTER,INST ANORGAN CHEM,W-4400 MUNSTER,GERMANY
关键词
AMINOCARBENE COMPLEXES OF IRON; N-VINYLAMINOCARBENE COMPLEXES; PI-ALLYL; SIGMA-COMPLEXES OF IRON; N-(2-PROPENYL)AMINOCARBENE COMPLEXES; METHYLENATION OF KETENE IMINES BY CARBENE COMPLEXES;
D O I
10.1002/cber.19911240816
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Ketene imines R(Me)C = C = NPh (2, R = Me, Et, i-Pr) form 1:1 adducts with the carbene iron complex (CO)4Fe = C(OEt)Ph (1). The initial step of the reaction involves an attack of the nitrogen atom of 2 at the carbene carbon atom of 1 and a subsequent rearrangement to give N-vinylaminocarbene complexes (E/Z)-4. In a parallel process with different regiochemistry the central carbon of the CCN unit is attached to the carbene carbon to yield pi-allyl, sigma-complexes (E/Z)-3. Alkylation of 3a with [Et3O]BF4 leads to the formation of a cationic N-(2-propenyl)-aminocarbene complex 6a. Protonation of 4 with trifluoroacetic acid results in a ring contraction to give the four-membered metallacycles 7. X-ray data are reported for prototypes (Z)-4c and 6a.
引用
收藏
页码:1795 / 1803
页数:9
相关论文
共 37 条
[1]   SYNTHESES AND REACTIVITY OF ORGANOMETALLIC COMPOUNDS CONTAINING IMINOACYL LIGANDS. REACTIONS OF METAL CARBONYL ANIONS WITH IMIDOYL HALIDES [J].
ADAMS, RD ;
CHODOSH, DF ;
GOLEMBESKI, NM ;
WEISSMAN, EC .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1979, 172 (02) :251-267
[2]  
ALVAREZTOLEDANO C, 1984, J CHEM SOC CHEM COMM, P574
[3]   STUDIES ON INTERACTIONS OF ISOCYANIDE WITH TRANSITION-METAL COMPLEXES .12. CRYSTAL AND MOLECULAR-STRUCTURE OF PI-C5H5FE(CO)[(C=NC6H11) (CNHC6H11)CH[CNHC(CH3)3]], A COMPLEX CONTAINING A BIDENTATE LIGAND BONDING TO AN IRON ATOM BY A SIGMA-BONDED GROUP AND A CARBENE GROUP [J].
AOKI, K ;
YAMAMOTO, Y .
INORGANIC CHEMISTRY, 1976, 15 (01) :48-52
[4]   ORGANIC SYNTHESES VIA TRANSITION-METAL COMPLEXES .51. 1-METALLA-1,3,5-TRIENES AND 1-METALLA-1,3-DIEN-5-YNES OF CHROMIUM AND TUNGSTEN BY INSERTION OF ALKYNES INTO M=C AND C=C BONDS OF 1-METALLA-1,3-DIENES AND 1-METALLA-1-EN-3-YNES, RESPECTIVELY [J].
AUMANN, R ;
HEINEN, H ;
HINTERDING, P ;
STRATER, N ;
KREBS, B .
CHEMISCHE BERICHTE, 1991, 124 (05) :1229-1236
[5]   ORGANIC SYNTHESES VIA TRANSITION-METAL COMPLEXES .36. MONOFUNCTIONAL TRI(METHYLENE)METHANE CHROMIUM AND IRON COMPLEXES BY ADDITION OF ALLENES TO M = C BONDS OF CARBENE COMPLEXES [J].
AUMANN, R ;
TRENTMANN, B .
CHEMISCHE BERICHTE-RECUEIL, 1989, 122 (10) :1977-1982
[7]  
AUMANN R, 1987, ANGEW CHEM, V99, P361
[8]   CYCLOPROPANES FROM REACTIONS OF TRANSITION-METAL CARBENE COMPLEXES WITH OLEFINS [J].
BROOKHART, M ;
STUDABAKER, WB .
CHEMICAL REVIEWS, 1987, 87 (02) :411-432
[9]   REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF VINYLCYCLOPROPANE DERIVATIVES FROM 1,3-DIENES AND A FISCHER CARBENE COMPLEX [J].
BUCHERT, M ;
REISSIG, HU .
TETRAHEDRON LETTERS, 1988, 29 (19) :2319-2320
[10]   SYNTHESIS AND X-RAY STRUCTURE OF CIS-TETRACARBONYL[(Z)-(ETA-2-ALLYLAMINO)(PARA-TOLYL)CARBENE]-TUNGSTEN(O), A STABLE METAL-CARBENE-ALKENE COMPLEX [J].
CASEY, CP ;
SHUSTERMAN, AJ ;
VOLLENDORF, NW ;
HALLER, KJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (09) :2417-2423