EurekaMag.com logo
+ Site Statistics
References:
53,214,146
Abstracts:
29,074,682
+ Search Articles
+ Subscribe to Site Feeds
EurekaMag Most Shared ContentMost Shared
EurekaMag PDF Full Text ContentPDF Full Text
+ PDF Full Text
Request PDF Full TextRequest PDF Full Text
+ Follow Us
Follow on FacebookFollow on Facebook
Follow on TwitterFollow on Twitter
Follow on Google+Follow on Google+
Follow on LinkedInFollow on LinkedIn

+ Translate

Regioselectivity in the nucleophile trapping of arynes: the electronic and steric effects of nucleophiles and substituents


Organic Letters 16(1): 6-9
Regioselectivity in the nucleophile trapping of arynes: the electronic and steric effects of nucleophiles and substituents
The regioselectivity in nucleophile trapping is investigated with arynes generated directly from bis-1,3-diynes. The regioselectivity is profoundly influenced by not only the nature of nucleophiles but also the substituents on the arynes, which is the consequence of both the unfavorable steric interaction between the incoming nucleophile and the nearby substituent and the inherent electronic bias induced by different substituents on the arynes.

(PDF same-day service: $19.90)

Accession: 055445952

PMID: 24313272

DOI: 10.1021/ol403237z



Related references

Steric and Electronic Substituent Effects Influencing Regioselectivity of Tetracene Endoperoxidation. Journal of Organic Chemistry 80(21): 11086-11091, 2015

Steric and electronic effects of methyl substituents at the 2 and 6 positions of n benzyl 1 4 dihydronicotinamide. Chemical & Pharmaceutical Bulletin (Tokyo) 35(7): 2661-2667, 1987

Control of regioselectivity by the lone substituent through steric and electronic effects in the nitrosoarene ene reaction of deuterium-labeled trisubstituted alkenes. Journal of Organic Chemistry 67(24): 8395-8399, 2002

Iron complexes for the catalytic transfer hydrogenation of acetophenone: steric and electronic effects imposed by alkyl substituents at phosphorus. Inorganic Chemistry 49(21): 10057-10066, 2011

Importance of allylic interactions and stereo electronic effects in dictating the steric course of the reaction of iminium ions with nucleophiles an efficient total synthesis of racemic gephyro toxin. Journal of the American Chemical Society 105(16): 5373-5379, 1983

Synthesis and pharmacology of 1-alkyl-3-(1-naphthoyl)indoles: steric and electronic effects of 4- and 8-halogenated naphthoyl substituents. Bioorganic & Medicinal Chemistry 20(6): 2067-2081, 2012

Effect of substituents on the GPx-like activity of ebselen: steric versus electronic. Journal of Physical Chemistry. A 112(5): 1013-1017, 2008

Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB(1) and CB(2) receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB(2) receptor agonists. Bioorganic & Medicinal Chemistry 13(1): 89-112, 2004

Effective chemiluminogenic systems based on acridinium esters bearing substituents of various electronic and steric properties. Organic & Biomolecular Chemistry 14(2): 652-668, 2015

Atropisomerism about aryl-Csp(3) bonds: the electronic and steric influence of ortho-substituents on conformational exchange in cannabidiol and linderatin derivatives. Journal of Organic Chemistry 79(13): 6015-6027, 2014