TY - JOUR
T1 - Chemical Behavior of 9-Cyclopentyl-9-borabarbaralane. Diverse Chemoselectivity in the Reactions with Methanol and Other Nucleophiles
AU - Gridnev, Ilya D.
AU - Meller, Anton
PY - 1998/5/29
Y1 - 1998/5/29
N2 - 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.
AB - 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.
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M3 - Article
AN - SCOPUS:1542602620
VL - 63
SP - 3599
EP - 3606
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 11
ER -