Synthesis of 2,6-Hexa-tert-butylterphenyl Derivatives, 2,6-(2,4,6-t-Bu3C6H2)2C6H3X, where X = I, Li, OH, SH, N3, or NH2

被引：13

作者：

Bukhryakov, Konstantin V. ^{[1
]}

Schrock, Richard R. ^{[1
]}

Hoveyda, Amir H. ^{[2
]}

Mueller, Peter ^{[1
]}

Becker, Jonathan ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

[2] Dept Chem, Boston Coll, Merkert Chem Ctr, Chestnut Hill, MA 02467 USA

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 10期

基金：

美国国家卫生研究院;

关键词：

OPENING METATHESIS POLYMERIZATION; SELECTIVE CROSS-METATHESIS; ALKYLIDENE COMPLEXES; 2,6-DIMESITYLPHENYLIMIDO LIGAND; OLEFIN METATHESIS; AROMATIC RING; MOLYBDENUM; TERPHENYL; HYDRIDE; CONTAIN;

D O I：

10.1021/acs.orglett.7b01062

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A "double benzyne" reaction between 1,3-dichloro-2-iodobenzene and 2,4,6-t-Bu3C6H2MgBr followed by the addition of iodine led to 2,6-(2,4,6-t-Bu3C6H2)(2)C6H3I (HTBTI) in 65% yield. Lithiation of HTBTI with Li-t-Bu gave Li(Et2O)(2)HTBT from which HTBTSH, HTBTN3, HTBTNH2, and HTBTOH were prepared. An X-ray structure of W(OHTBT)(2)Cl-4 shows that the two HTBTO ligands are trans to one another with t-Bu3C6H2; groups on one HTBTO interdigitated with the t-Bu3C6H2 groups on the other HTBTO.

引用

收藏

页码：2607 / 2609

页数：3

相关论文

共 42 条

[1] Stereospecific Ring-Opening Metathesis Polymerization (ROMP) of endo-Dicyclopentadiene by Molybdenum and Tungsten Catalysts [J].

Autenrieth, Benjamin ;

Jeong, Hyangsoo ;

Forrest, William P. ;

Axtell, Jonathan C. ;

Ota, Antje ;

Lehr, Thomas ;

Buchmeiser, Michael R. ;

Schrock, Richard R. .

MACROMOLECULES, 2015, 48 (08) :2480-2492

[2] Stereospecific Ring-Opening Metathesis Polymerization (ROMP) of Norbornene and Tetracyclododecene by Mo and W Initiators [J].

Autenrieth, Benjamin ;

Schrock, Richard R. .

MACROMOLECULES, 2015, 48 (08) :2493-2503

[3] Synthesis of Molybdenum and Tungsten Alkylidene Complexes That Contain the 2,6-Bis(2,4,6-triisopropylphenyl)phenylimido (NHIPT) Ligand [J].

Axtell, Jonathan C. ;

Schrock, Richard R. ;

Mueller, Peter ;

Hoveyda, Amir H. .

ORGANOMETALLICS, 2015, 34 (11) :2110-2113

[4] Synthesis and characterization of the monomeric molybdenum trithiolate Mo(η7-dmpt)(η1-dmpt)2 (dmpt = 2,6-dimesitylphenylthiolate) [J].

Buyuktas, BS ;

Olmstead, MM ;

Power, PP .

CHEMICAL COMMUNICATIONS, 1998, (16) :1689-1690

[5] KINETICS AND MECHANISM OF REACTION OF IODINE WITH TETRAHYDROFURAN . A CARBON-HYDROGEN BOND DISSOCIATION ENERGY IN TETRAHYDROFURAN [J].

CRUICKSHANK, FR ;

BENSON, SW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (06) :1289-+

[6] A ONE-POT SYNTHESIS OF M-TERPHENYLS VIA A 2-ARYNE SEQUENCE [J].

DU, CJF ;

HART, H ;

NG, KKD .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (16) :3162-3165

[7]

Ellison J.J., 1994, Angew. Chem, V106, P1248

[8] Tungsten Oxo Alkylidene Complexes as Initiators for the Stereoregular Polymerization of 2,3-Dicarbomethoxynorbornadiene [J].

Forrest, William P. ;

Axtell, Jonathan C. ;

Schrock, Richard R. .

ORGANOMETALLICS, 2014, 33 (09) :2313-2325

[9] Synthesis and reactivity of alkyl, hydride, and silyl derivatives of the (terphenyl)imido fragments Cp*(ArMesN=)Ta (Cp* = η5-C5Me5;: ArMes=2,6-(2,4,6-Me3C6H2)2C6H3) and Cp*(ArTripN=)Ta (ArTrip=2,6-(2,4,6-iPr3C6H2)2C6H3) [J].

Gavenonis, J ;

Tilley, TD .

ORGANOMETALLICS, 2004, 23 (01) :31-43

[10] Tantalum alkyl and silyl complexes of the bulky (terphenyl)imido ligand [2,6-(2,4,6-Me3C6H2)2C6H3N=]2-([Ar*N=]2-).: Generation and reactivity of [(Ar*N=)(Ar*NH)Ta(H)(OSO2CF3)], which reversibly transfers hydride to an aromatic ring of the arylamide ligand [J].

Gavenonis, J ;

Tilley, TD .

ORGANOMETALLICS, 2002, 21 (25) :5549-5563

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