CHEMICAL BEHAVIOR OF 9-CYCLOPENTYL-9-BORABARBARALANE - DIVERSE CHEMOSELECTIVITY IN THE REACTIONS WITH METHANOL AND OTHER NUCLEOPHILES

Authors
GRIDNEV ID MELLER A
Citation
Id. Gridnev et A. Meller, CHEMICAL BEHAVIOR OF 9-CYCLOPENTYL-9-BORABARBARALANE - DIVERSE CHEMOSELECTIVITY IN THE REACTIONS WITH METHANOL AND OTHER NUCLEOPHILES, Journal of organic chemistry, 63(11), 1998, pp. 3599-3606
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
63
Issue
11
Year of publication
1998
Pages
3599 - 3606
Database
ISI
SICI code
0022-3263(1998)63:11<3599:CBO9-D>2.0.ZU;2-C
Abstract
The 9-cyclopentyl-9-borabarbaralane (3e) was obtained by the reaction of K2C8H8 with cyclo-C5H9BCl2. Upon reaction of 3e with acetone, aceta ldehyde, ethoxyacetylene, trideuterioacetonitrile, and acetic acid, on ly products derived from -cyclopentyl-9-borabicyclo[4.2.1]nona-2,4,7-t riene (1e) were obtained. On the other hand, by methanolysis of 3e, th e boronic ester 17 was formed. The tetracyclic borane 18 is proposed a s the intermediate. Possible reasons for this unusual chemical behavio r are discussed.