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

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

doi:10.1039/p19750000579

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

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

Research output: Contribution to journal › Article › peer-review

35 Scopus citations

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 language	English (US)
Pages (from-to)	579-588
Number of pages	10
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	6
DOIs	https://doi.org/10.1039/p19750000579
State	Published - 1975
Externally published	Yes

ASJC Scopus subject areas

General Chemistry

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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.",

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AU - Bracho, Ruben D.

AU - Gunatilaka, A. A.Leslie

AU - Widdowson, David A.

PY - 1975

Y1 - 1975

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AB - 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.

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ER -

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

Abstract

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