Reaction of Methylidenecycloalkanes with BF3•THF Catalyzed by Cp2TiCl2

被引：2

作者：

Tulyabaeva, L. I. ^{[1
]}

Salakhutdinov, R. R. ^{[1
]}

Tulyabaev, A. R. ^{[1
]}

Tyumkina, T. V. ^{[1
]}

Abdullin, M. F. ^{[2
]}

机构：

[1] Russian Acad Sci, Inst Petrochem & Catalysis, Ufa Fed Res Ctr, Ufa 450075, Russia

[2] Russian Acad Sci, Ufa Inst Chem, Ufa Fed Res Ctr, Ufa 450054, Russia

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 58卷 / 12期

关键词：

methylidenecycloalkanes; cycloboration; isomerization; spiro-boracarbocycles; BF3; THF; Cp2TiCl2; ALPHA-OLEFINS; BORON; COMPLEXES; CYCLOBORATION; CHEMISTRY; ALKYNES;

D O I：

10.1134/S1070428022120296

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of methylidenecycloalkanes with BF3 center dot THF in the presence of Cp2TiCl2 as catalyst has been performed for the first time to obtain 1-fluoroboriranes spiro-fused to cycloalkanes and 1-methylcycloalk-1-enes formed as a result of isomerization of the initial olefin. The product structure was confirmed by one- (H-1, C-13 DEPT, B-11, F-19) and two-dimensional (COSY, HSQC, HMBC) NMR and mass spectra in combination with quantum chemical calculation of C-13 chemical shifts.

引用

页码：1976 / 1983

页数：8

共 43 条

[1] Unusual temperature dependence in the cis/trans-oxetane formation discloses competitive syn versus anti attack for the Paterno-Buchi reaction of triplet-excited ketones with cis- and trans-cyclooctenes.: Conformational control of diastereoselectivity in the cyclization and cleavage of preoxetane diradicals [J].

Adam, W ;

Stegmann, VR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (14) :3600-3607

[2] CHLOROMETHYL-LITHIUM AND 1-CHLORO-2-METHYLPROP-1-ENYL-LITHIUM - USEFUL INTERMEDIATES IN THE SYNTHESIS OF UNSATURATED AND BIFUNCTIONALIZED COMPOUNDS [J].

BARLUENGA, J ;

FERNANDEZSIMON, JL ;

CONCELLON, JM ;

YUS, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (12) :3339-3343

[3] Modern applications of low-valent early transition metals in synthesis and catalysis [J].

Beaumier, Evan P. ;

Pearce, Adam J. ;

See, Xin Yi ;

Tonks, Ian A. .

NATURE REVIEWS CHEMISTRY, 2019, 3 (01) :15-34

[4] The Pauson-Khand reaction, a powerful synthetic tool for the synthesis of complex molecules [J].

Blanco-Urgoiti, J ;

Añorbe, L ;

Pérez-Serrano, L ;

Domínguez, G ;

Pérez-Castells, J .

CHEMICAL SOCIETY REVIEWS, 2004, 33 (01) :32-42

[5] Titanium redox catalysis: insights and applications of an earth-abundant base metal [J].

Davis-Gilbert, Zachary W. ;

Tonks, Ian A. .

DALTON TRANSACTIONS, 2017, 46 (35) :11522-11528

[6] Boron-containing small rings: synthesis, properties, and application prospects [J].

Dzhemilev, U. M. ;

Khusainova, L. I. ;

Ryazanov, K. S. ;

Khafizova, L. O. .

RUSSIAN CHEMICAL BULLETIN, 2021, 70 (10) :1851-1892

[7] Bromo-boronolactonization of olefins [J].

Falck, JR ;

Bondlela, M ;

Venkataraman, SK ;

Srinivas, D .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (21) :7148-7150

[8] THE WITTIG REACTION USING POTASSIUM-TERT-BUTOXIDE HIGH-YIELD METHYLENATIONS OF STERICALLY HINDERED KETONES [J].

FITJER, L ;

QUABECK, U .

SYNTHETIC COMMUNICATIONS, 1985, 15 (10) :855-864

[9]

Frisch M., 2009, Gaussian 09 Revision E.1., DOI DOI 10.1002/JCC.22885

[10] Cationic Titanocene(III) Complexes for Catalysis in Single-Electron Steps [J].

Gansaeuer, Andreas ;

Hildebrandt, Sven ;

Michelmann, Antonius ;

Dahmen, Tobias ;

von Laufenberg, Daniel ;

Kube, Christian ;

Fianu, Godfred D. ;

Flowers, Robert A., II .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (24) :7003-7006

← 1 2 3 4 5 →