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

34 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

Access to Document

10.1039/p19750000579

Cite this

@article{85f1d3c5d7d94886b138e99cb536379e,

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

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.",

author = "Barton, {Derek H.R.} and Bracho, {Ruben D.} and Gunatilaka, {A. A.Leslie} and Widdowson, {David A.}",

year = "1975",

doi = "10.1039/p19750000579",

language = "English (US)",

pages = "579--588",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

issn = "1472-7781",

publisher = "Chemical Society",

number = "6",

}

TY - JOUR

T1 - Phenol oxidation and biosynthesis. Part XXV. New syntheses of bis-(2-arylethyl)amines of biosynthetic importance

AU - Barton, Derek H.R.

AU - Bracho, Ruben D.

AU - Gunatilaka, A. A.Leslie

AU - Widdowson, David A.

PY - 1975

Y1 - 1975

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=37049125308&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=37049125308&partnerID=8YFLogxK

U2 - 10.1039/p19750000579

DO - 10.1039/p19750000579

M3 - Article

AN - SCOPUS:37049125308

SN - 1472-7781

SP - 579

EP - 588

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 6

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this