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Geminal bis-borane formation by borane Lewis acid induced cyclopropyl rearrangement and its frustrated Lewis pair reaction with carbon dioxide.

ABSTRACT: Cyclopropylacetylene reacts with two molar equivalents of Piers' borane [HB(C6F5)2] under mild conditions by an addition/rearrangement sequence with cyclopropyl ring opening to give a mixture of two ?-B(C6F5)2 substituted tetrahydroboroles. This compound forms an active frustrated Lewis pair with P t Bu3 that heterolytically splits dihydrogen and adds carbon dioxide as a geminal chelate bis-boryl component. The respective reactions of the two-fold HB(C6F5)2 addition to Ph-CH2CH2C 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 1111111111111111111111111111111111 1111111111111111111111111111111111 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 1111111111111111111111111111111111 1111111111111111111111111111111111 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 1111111111111111111111111111111111 1111111111111111111111111111111111 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 CH were studied as a geminal Lewis acid reference. Most of the products were characterized by X-ray diffraction.

SUBMITTER: Liu YL 

PROVIDER: S-EPMC5369401 | biostudies-literature | 2017 Feb

REPOSITORIES: biostudies-literature

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Geminal bis-borane formation by borane Lewis acid induced cyclopropyl rearrangement and its frustrated Lewis pair reaction with carbon dioxide.

Liu Yun-Lin YL   Kehr Gerald G   Daniliuc Constantin G CG   Erker Gerhard G  

Chemical science 20160916 2

Cyclopropylacetylene reacts with two molar equivalents of Piers' borane [HB(C<sub>6</sub>F<sub>5</sub>)<sub>2</sub>] under mild conditions by an addition/rearrangement sequence with cyclopropyl ring opening to give a mixture of two α-B(C<sub>6</sub>F<sub>5</sub>)<sub>2</sub> substituted tetrahydroboroles. This compound forms an active frustrated Lewis pair with P <sup><i>t</i></sup> Bu<sub>3</sub> that heterolytically splits dihydrogen and adds carbon dioxide as a geminal chelate bis-boryl compo  ...[more]

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