NDLI: Electrophilic aromatic addition reaction: electrophilic attack at an aromatic H substituent position.

Content Provider	Semantic Scholar
Author	Choi, Han Young Srisook, Ekaruth Jang, Kun Sam Chi, Dae Yoon
Copyright Year	2005
Abstract	[reaction: see text] We report and propose a mechanism for an unusual electrophilic aromatic addition reaction (Ad(E)()Ar). During our preparation of 5,7-dibromo-8-methoxyquinaldine as a key intermediate in the synthesis of 7-bromoquinaldine-5,8-dione, direct bromination in either acidic or neutral conditions led only to the formation of 5-bromo-8-methoxyquinaldine. Under basic methanolic conditions, however, we unexpectedly obtained the 5,7-dibromo-8,8-dimethoxy-7,8-dihydroquinaldine adduct 2a. This result not only allows for the functionalization of aromatic compounds via the addition adducts, but also introduces the possibility of an alternate mechanism for electrophilic substitution reactions.
File Format	PDF HTM / HTML
DOI	10.1021/jo048297x
Alternate Webpage(s)	http://www.thaiscience.info/Article%20for%20ThaiScience/Article/61/10008897.pdf
PubMed reference number	15704954
Alternate Webpage(s)	https://doi.org/10.1021/jo048297x
Journal	Medline
Volume Number	70
Issue Number	4
Journal	The Journal of organic chemistry
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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