Cp2TiCl2-Catalyzed Interaction of Methylenecycloalkane with BF3·THF

Мұқаба

Дәйексөз келтіру

Толық мәтін

Ашық рұқсат Ашық рұқсат
Рұқсат жабық Рұқсат берілді
Рұқсат жабық Тек жазылушылар үшін

Аннотация

The Cp2TiCl2-catalyzed interaction of methylenecycloalkanes with BF3·THF in tetrahydrofuran was carried out for the first time with the formation of target 1-fluoro-1-boraspirocarbocycles and also isomerization products of a starting monomer (1-methylcycloalk-1-enes). The structure of reaction products was elucidated using one- (1H, 13C Dept, 11B, 19F) and two-dimensional (COSY, HSQC, HMBC) NMR spectroscopy, mass spectrometry combined with quantum-chemical calculations of 13C NMR chemical shifts.

Толық мәтін

Рұқсат жабық

Авторлар туралы

L. Tulyabaeva

Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences

Хат алмасуға жауапты Автор.
Email: khusainova_ink@mail.ru
ORCID iD: 0000-0002-3159-2868
Ресей, Ufa

R. Salakhutdinov

Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences

Email: khusainova_ink@mail.ru
ORCID iD: 0000-0003-3631-0708
Ресей, Ufa

A. Tulyabaev

Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences

Email: khusainova_ink@mail.ru
ORCID iD: 0000-0002-6566-4794
Ресей, Ufa

T. Tyumkina

Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences

Email: khusainova_ink@mail.ru
ORCID iD: 0000-0001-8127-9135
Ресей, Ufa

M. Abdullin

Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences

Email: khusainova_ink@mail.ru
ORCID iD: 0000-0002-9894-213X
Ресей, Ufa

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Әрекет
1. JATS XML
Жүктеу
2. Scheme 1. Cp2TiCl2-catalyzed synthesis of 1,2-disubstituted boriranes 1,2.

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3. Scheme 2. Interaction of α-olefins with BF3 THF under the action of Cp2TiCl2.

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4. Scheme 3. α,ω-Dienes in Cp2TiCl2-catalyzed synthesis of boriranes.

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5. Scheme 4. Proposed scheme for the formation of a titanium hydride complex.

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6. Scheme 5. Proposed scheme for the formation of spiroborocarbocycles by the reaction of methylenecycloalkanes with BHal3 under the action of Cp2TiCl2.

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7. Scheme 6. Oxidation of 1-fluoro-substituted boraspirane 7.

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8. Scheme 7. Cp2TiCl2-catalyzed interaction of methylenecyclododecane with BF3·THF.

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9. Scheme 8. Cp2TiCl2-catalyzed interaction of methylenecycloalkanes with BF3 THF

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10. Fig. 1. NMR spectra 11B (a) and 19F (b) of the reaction mixture after the interaction of methylenecyclododecane with BF3 THF in the presence of Cp2TiCl2/Mg (CDCl3, 298 K)

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11. Fig. 2. Mass spectrum of organoboron compound 8

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12. Fig. 3. NMR spectra 1H (a) and 13C (b) (together with 13C DEPTQ) of the reaction mixture after the interaction of methylenecyclododecane with BF3 THF in the presence of Cp2TiCl2/Mg (CDCl3, 298 K)

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13. Fig. 4. HSQC (a) and HMBC (fragment) (b) experiments of the reaction mixture after the interaction of methylenecyclododecane with BF3 THF in the presence of Cp2TiCl2/Mg

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14. Fig. 5. Mass spectrum of 1-methylcyclododec-1-ene 9

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15. Fig. 6. Structure of (Z/E)-isomers of 1-methylcyclododec-1-ene optimized by the B3LYP/cc-pVDZ method (13C NMR chemical shifts are given in ppm)

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