Chemical Behavior of 9-Cyclopentyl-9-borabarbaralane. Diverse Chemoselectivity in the Reactions with Methanol and Other Nucleophiles

Ilya D. Gridnev, Anton Meller

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

The 9-cyclopentyl-9-borabarbaralane (3e) was obtained by the reaction of K2C8H8 with cyclo-C5H9BCl2. Upon reaction of 3e with acetone, acetaldehyde, ethoxyacetylene, trideuterioacetonitrile, and acetic acid, only products derived from 9-cyclopentyl-9-borabicyclo[4.2.1]nona-2,4,7-triene (1e) were obtained. On the other hand, by methanolysis of 3e, the boronic ester 17 was formed. The tetracyclic borane 18 is proposed as the intermediate. Possible reasons for this unusual chemical behavior are discussed.

Original languageEnglish
Pages (from-to)3599-3606
Number of pages8
JournalJournal of Organic Chemistry
Volume63
Issue number11
Publication statusPublished - 1998 May 29
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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