STOICHIOMETRIC REACTION OF TITANACYCLOPENTADIENE COMPOUNDS WITH ALLYLIC ETHERS - REGIOCHEMISTRY OF METHYLENECYCLOHEX-3-ENE FORMATION

被引：13

作者：

BALAICH, GJ ^{[1
]}

ROTHWELL, IP ^{[1
]}

机构：

[1] PURDUE UNIV, DEPT CHEM, W LAFAYETTE, IN 47907 USA

来源：

TETRAHEDRON | 1995年 / 51卷 / 15期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/0040-4020(94)01133-K

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The titanacyclopentadiene complexes [(ArO)(2)Ti(C(4)Et(4))] (1a), [(ArO)(2)Ti(C(4)Et(2)(CH2)(4))] (1b) and [(ArO)(2)Ti(C(4)Bu(2)(t)H(2))] (1c) (ArO = 2,6-diphenylphenoxide) react with allylphenylether to produce new organometallic products containing cyclohexadiene-methyl and phenoxide ligands. Hydrolysis of these compounds leads to the formation of single regioisomers of substituted methylenecyclohex-3-ene along with two equivalents of 2,6-diphenylphenol and one equivalent of phenol. A reaction sequence involving initial (2+2+2) cycloaddition followed by cleavage of a phenyl ether bond is discussed.

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页码：4463 / 4470

页数：8

相关论文

共 23 条

[1] REGIOSELECTIVE AND STEREOSELECTIVE FORMATION AND ISOMERIZATION OF 1,3-CYCLOHEXADIENES CATALYZED BY TITANIUM ARYLOXIDE COMPOUNDS [J].

BALAICH, GJ ;

ROTHWELL, IP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (04) :1581-1583

[2] INSERTION REACTIONS OF NITRILES IN CATIONIC ALKYLBIS(CYCLOPENTADIENYL)TITANIUM COMPLEXES - THE FACILE SYNTHESIS OF AZAALKENYLIDENE TITANIUM COMPLEXES AND THE CRYSTAL AND MOLECULAR-STRUCTURE OF [(INDENYL)2TI(NCMEPH)(NCPH)]BPH4 [J].

BOCHMANN, M ;

WILSON, LM ;

HURSTHOUSE, MB ;

MOTEVALLI, M .

ORGANOMETALLICS, 1988, 7 (05) :1148-1154

[3]

Cardin D. J., 1986, CHEM ORGANOZIRCONIUM

[4] INTRAMOLECULAR COUPLING OF ETA-2-IMINOACYL AND ETA-2-ACYL FUNCTIONS AT GROUP-4 AND GROUP-5 METAL CENTERS - STRUCTURE AND SPECTROSCOPIC PROPERTIES OF THE RESULTING ENAMIDOLATE AND ENEDIAMIDE COMPLEXES [J].

CHAMBERLAIN, LR ;

DURFEE, LD ;

FANWICK, PE ;

KOBRIGER, LM ;

LATESKY, SL ;

MCMULLEN, AK ;

STEFFEY, BD ;

ROTHWELL, IP ;

FOLTING, K ;

HUFFMAN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (20) :6068-6076

[5] ISOSPECIFIC POLYMERIZATION OF PROPYLENE CATALYZED BY RAC-ETHYLENEBIS(INDENYL)METHYLZIRCONIUM CATION [J].

CHIEN, JCW ;

TSAI, WM ;

RAUSCH, MD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) :8570-8571

[6] FORMATION AND CHARACTERIZATION OF ETA-2-IMINE AND ETA-2-AZOBENZENE DERIVATIVES OF TITANIUM CONTAINING ANCILLARY ARYLOXIDE LIGATION [J].

DURFEE, LD ;

HILL, JE ;

FANWICK, PE ;

ROTHWELL, IP .

ORGANOMETALLICS, 1990, 9 (01) :75-80

[7] INTRAMOLECULAR COUPLING OF ETA-2-IMINOACYL GROUPS AT GROUP-4 METAL CENTERS - A KINETIC-STUDY OF THE CARBON CARBON DOUBLE-BOND-FORMING REACTION [J].

DURFEE, LD ;

MCMULLEN, AK ;

ROTHWELL, IP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) :1463-1467

[8] ISOLATION AND CHARACTERIZATION OF TI(O)(OAR-2,6PRI2)2(NC5H4-4NC4H8)2(OAR-2,6PRI2=2,6-DIISOPROPYLPHENOXIDE - NC5H4-4NC4H8=4-PYRROLIDINOPYRIDINE) - A MONONUCLEAR ARYLOXIDE COMPOUND CONTAINING A TERMINAL TITANIUM(IV)-OXO GROUP [J].

HILL, JE ;

FANWICK, PE ;

ROTHWELL, IP .

INORGANIC CHEMISTRY, 1989, 28 (18) :3602-3604

[9] SYNTHESIS, STRUCTURE, AND REACTIVITY OF A NEW SERIES OF TITANIUM ETA-2-OLEFIN AND ETA-2-KETONE COMPLEXES [J].

HILL, JE ;

FANWICK, PE ;

ROTHWELL, IP .

ORGANOMETALLICS, 1992, 11 (05) :1771-1773

[10] FORMATION, FRAGMENTATION, AND ISOMERIZATION OF TITANACYCLE RINGS SUPPORTED BY ARYLOXIDE LIGATION [J].

HILL, JE ;

FANWICK, PE ;

ROTHWELL, IP .

ORGANOMETALLICS, 1990, 9 (08) :2211-2213