COMPATIBILITY OF VARIOUS CARBANION NUCLEOPHILES WITH HETEROAROMATIC NUCLEOPHILIC-SUBSTITUTION BY THE S(RN)1 MECHANISM

Authors
WONG JW NATALIE KJ NWOKOGU GC PISIPATI JS FLAHERTY PT GREENWOOD TD WOLFE JF
Citation
Jw. Wong et al., COMPATIBILITY OF VARIOUS CARBANION NUCLEOPHILES WITH HETEROAROMATIC NUCLEOPHILIC-SUBSTITUTION BY THE S(RN)1 MECHANISM, Journal of organic chemistry, 62(18), 1997, pp. 6152-6159
Citations number
55
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
62
Issue
18
Year of publication
1997
Pages
6152 - 6159
Database
ISI
SICI code
0022-3263(1997)62:18<6152:COVCNW>2.0.ZU;2-L
Abstract
Carbanions generated from 2,4,4-trimethyl-2-oxazoline (1a), 2-benzyl-4 ,4-dimethyl-2-oxazoline (1b), 2,4-dimethylthiazole (13a), 2-benzyl-4-m ethylthiazole (13b), N,N-dimethylacetamide (17a), tert-butyl acetate ( 17b), ethyl phenylacetate (17c), N-methyl-N-phenyl-2-butenamide (22), tert-butyl 3-butenoate (25), and dimethyl methylphosphonate (29a) by m eans of KNH2 in liquid NH3 all reacted with 2-bromopyridine (2) via ph otoassisted reactions that exhibited characteristics of the S(RN)1 mec hanism. Similar results were obtained in reactions of these carbanions with other substrates, including 2-chloroquinoline (6), iodobenzene ( 9), bromobenzene (10), and bromomesitylene (11).