Unusual chemical behavior of 9,10-dipropyl-10-borabicyclodeca-2,4,7-triene, heteroanalog of (CH)10 hydrocarbons

Ilya D. Gridnev, Mikhail E. Gurskii, Alexei V. Buevich, Tamara V. Potapova, Yuri N. Bubnov

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The title compound 1 selectively gives products with completely different carbon skeletons in various reactions. Thus, thermolysis of 1 provides tricyclic borane 4, oxidation leads to the compounds 5, 6 (in a 5:1 ratio) with cyclooctatriene structure, methanolysis followed by oxidation yields bicyclic alcohol 7, and the reaction of 1 with acetone leads to the product with the cycloheptadiene skeleton 8. Such unusual chemical behavior of 1 can be rationalized by its coexistense with minor valence tautomers 12, 17, 18, 22.

Original languageEnglish
Pages (from-to)3514-3519
Number of pages6
JournalJournal of Organic Chemistry
Volume61
Issue number10
DOIs
Publication statusPublished - 1996 May 17
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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