Phenol oxidation and biosynthesis. Part XXV. New syntheses of bis-(2-arylethyl)amines of biosynthetic importance

Derek H R Barton, Ruben D. Bracho, Leslie Gunatilaka, David A. Widdowson

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

Two efficient routes to bis-(2-arylethyl)amines have been developed by using regiospecific alkylation of dialkylnitrosamine anions and homologation of aromatic aldehydes with methoxyacetonitrile anion as the respective key steps. The hitherto uncharacterised 1,3-diaryl-2-azonia-allene ions have been prepared in isolable form. Attempted insertion of C1 fragments into these systems as a third route to the title compounds failed.

Original languageEnglish (US)
Pages (from-to)579-588
Number of pages10
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number6
StatePublished - 1975
Externally publishedYes

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Biosynthesis
Phenol
Amines
Anions
Oxidation
Alkylation
Aldehydes
Ions
propadiene

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Phenol oxidation and biosynthesis. Part XXV. New syntheses of bis-(2-arylethyl)amines of biosynthetic importance. / Barton, Derek H R; Bracho, Ruben D.; Gunatilaka, Leslie; Widdowson, David A.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 6, 1975, p. 579-588.

Research output: Contribution to journalArticle

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