An improved, easy and efficient method for the generation of nitrite oxides from nitronates for in situ 1,3-dipolar cycloaddition

Jing Yuan Liu, Ming Chung Yan, Wen-Wei Lin, Lian Yong Wang, Ching-Fa Yao

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The Michael addition of the diethyl allyl malonate anion to β-nitrostyrenes l generated nitronates 5. Nitronates 5 could be converted into nitrile oxides 7 to undergo intramolecular nitrite oxide-olefin cycloaddition (INOC) to form medium to high yields (51-95%) of five-membered carbocycles 8 and 9 by using ethyl chloroformate in the presence of a catalytic amount of 4-dimethylaminopyridine (DMAP). High yields (91%) of tricyclic compounds 11 and 12 were obtained when la reacted with the anion of 10 under similar experimental conditions and procedures.

Original languageEnglish
Pages (from-to)1215-1218
Number of pages4
JournalJournal of the Chemical Society - Perkin Transactions 1
Issue number9
DOIs
Publication statusPublished - 1999 Jan 1

Fingerprint

Cycloaddition
Nitrites
Oxides
Anions
Nitriles
Alkenes
ethyl chloroformate
4-dimethylaminopyridine
malonic acid

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

An improved, easy and efficient method for the generation of nitrite oxides from nitronates for in situ 1,3-dipolar cycloaddition. / Liu, Jing Yuan; Yan, Ming Chung; Lin, Wen-Wei; Wang, Lian Yong; Yao, Ching-Fa.

In: Journal of the Chemical Society - Perkin Transactions 1, No. 9, 01.01.1999, p. 1215-1218.

Research output: Contribution to journalArticle

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