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Halogenoborane mediated allene cyclooligomerization.


ABSTRACT: The halogenoboranes XB(C6F5)2 (X: Cl, Br) react with allene to give a mixture of the cyclotrimer 1,3,5-trimethylenecyclohexane (1) and the related halogenoborylated cyclotetramerization products 3a and 3b. Alkyl-substituted allenes were catalytically cyclotrimerized metal-free by XB(C6F5)2 (X: Cl, Br) to give cis,trans-2,4,6-trialkyl-1,3,5-trimethylenecyclohexanes under mild conditions.

SUBMITTER: Tao X 

PROVIDER: S-EPMC6385850 | biostudies-other | 2019 Feb

REPOSITORIES: biostudies-other

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Halogenoborane mediated allene cyclooligomerization.

Tao Xin X   Wölke Christian C   Daniliuc Constantin G CG   Kehr Gerald G   Erker Gerhard G  

Chemical science 20190102 8


The halogenoboranes XB(C<sub>6</sub>F<sub>5</sub>)<sub>2</sub> (X: Cl, Br) react with allene to give a mixture of the cyclotrimer 1,3,5-trimethylenecyclohexane (<b>1</b>) and the related halogenoborylated cyclotetramerization products <b>3a</b> and <b>3b</b>. Alkyl-substituted allenes were catalytically cyclotrimerized metal-free by XB(C<sub>6</sub>F<sub>5</sub>)<sub>2</sub> (X: Cl, Br) to give <i>cis</i>,<i>trans</i>-2,4,6-trialkyl-1,3,5-trimethylenecyclohexanes under mild conditions. ...[more]

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