volume 16 issue 1 pages 61-64

Vicarious Nucleophilic Substitution of Hydrogen versus Bis-Annulation in the Reaction of Chloromethyl Aryl Sulfone Carbanion with Electrophilic Arenes

Mieczyslaw M\kakosza
Tomasz Glinka
Stanislaw Ostrowski
Andrzej Rykowski
Publication typeJournal Article
Publication date1987-01-05
scimago Q3
wos Q4
SJR0.374
CiteScore2.8
Impact factor1.1
ISSN03667022, 13480715
General Chemistry
Abstract
The carbanion of chloromethyl aryl sulfone reacts with 1-cyanonaphthalene to form a bis-annulated product whereas with 1-nitronaphthalene vicarious nucleophilic substitution of hydrogen takes place. This result and the bis-annulation of quinoxalines and naphthyridines which was reported earlier are rationalized in terms of the negative charge delocalization in the intermediate σ-adducts.
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GOST Copy
M\kakosza M. et al. Vicarious Nucleophilic Substitution of Hydrogen versus Bis-Annulation in the Reaction of Chloromethyl Aryl Sulfone Carbanion with Electrophilic Arenes // Chemistry Letters. 1987. Vol. 16. No. 1. pp. 61-64.
GOST all authors (up to 50) Copy
M\kakosza M., Glinka T., Ostrowski S., Rykowski A. Vicarious Nucleophilic Substitution of Hydrogen versus Bis-Annulation in the Reaction of Chloromethyl Aryl Sulfone Carbanion with Electrophilic Arenes // Chemistry Letters. 1987. Vol. 16. No. 1. pp. 61-64.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1246/cl.1987.61
UR - https://doi.org/10.1246/cl.1987.61
TI - Vicarious Nucleophilic Substitution of Hydrogen versus Bis-Annulation in the Reaction of Chloromethyl Aryl Sulfone Carbanion with Electrophilic Arenes
T2 - Chemistry Letters
AU - M\kakosza, Mieczyslaw
AU - Glinka, Tomasz
AU - Ostrowski, Stanislaw
AU - Rykowski, Andrzej
PY - 1987
DA - 1987/01/05
PB - Oxford University Press
SP - 61-64
IS - 1
VL - 16
SN - 0366-7022
SN - 1348-0715
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{1987_M\kakosza,
author = {Mieczyslaw M\kakosza and Tomasz Glinka and Stanislaw Ostrowski and Andrzej Rykowski},
title = {Vicarious Nucleophilic Substitution of Hydrogen versus Bis-Annulation in the Reaction of Chloromethyl Aryl Sulfone Carbanion with Electrophilic Arenes},
journal = {Chemistry Letters},
year = {1987},
volume = {16},
publisher = {Oxford University Press},
month = {jan},
url = {https://doi.org/10.1246/cl.1987.61},
number = {1},
pages = {61--64},
doi = {10.1246/cl.1987.61}
}
MLA
Cite this
MLA Copy
M\kakosza, Mieczyslaw, et al. “Vicarious Nucleophilic Substitution of Hydrogen versus Bis-Annulation in the Reaction of Chloromethyl Aryl Sulfone Carbanion with Electrophilic Arenes.” Chemistry Letters, vol. 16, no. 1, Jan. 1987, pp. 61-64. https://doi.org/10.1246/cl.1987.61.