One-Pot Anodic Conversion of Symmetrical Bisamides of Ethylene Diamine to Unsymmetrical gem-Bisamides of Methylene Diamine

Tatiana Golub; Gui Yuan Dou; Cheng Chu Zeng; James Y. Becker

doi:10.1021/acs.orglett.9b02917

One-Pot Anodic Conversion of Symmetrical Bisamides of Ethylene Diamine to Unsymmetrical gem-Bisamides of Methylene Diamine

Tatiana Golub, Gui Yuan Dou, Cheng Chu Zeng, James Y. Becker

Department of Chemistry

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

10 Scopus citations

Abstract

Symmetrical bisamides of ethylene diamine of type ArCONHCH₂CH₂NHCOAr undergo anodic C-C bond cleavage in acetonitrile-LiClO₄ under controlled-potential electrolysis. The electrogenerated carbocation intermediates react with the solvent acetonitrile to afford unsymmetrical gem-bisamides of type ArCONHCH₂NHCOMe in a one-pot reaction. The yields of the latter products are moderate (up to 60%). Other minor products involve two symmetrical gem-bisamides of type ArCONHCH₂NHCOAr and MeCONHCH₂NHCOMe and fragmentation products (e.g., ArCONHCHO, ArCONH₂, and ArCN).

Original language	English
Pages (from-to)	7961-7964
Number of pages	4
Journal	Organic Letters
Volume	21
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.9b02917
State	Published - 4 Oct 2019

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.9b02917

Cite this

@article{ae277402f08943759727996cd6069e46,

title = "One-Pot Anodic Conversion of Symmetrical Bisamides of Ethylene Diamine to Unsymmetrical gem-Bisamides of Methylene Diamine",

abstract = "Symmetrical bisamides of ethylene diamine of type ArCONHCH2CH2NHCOAr undergo anodic C-C bond cleavage in acetonitrile-LiClO4 under controlled-potential electrolysis. The electrogenerated carbocation intermediates react with the solvent acetonitrile to afford unsymmetrical gem-bisamides of type ArCONHCH2NHCOMe in a one-pot reaction. The yields of the latter products are moderate (up to 60%). Other minor products involve two symmetrical gem-bisamides of type ArCONHCH2NHCOAr and MeCONHCH2NHCOMe and fragmentation products (e.g., ArCONHCHO, ArCONH2, and ArCN).",

author = "Tatiana Golub and Dou, {Gui Yuan} and Zeng, {Cheng Chu} and Becker, {James Y.}",

note = "Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = oct,

day = "4",

doi = "10.1021/acs.orglett.9b02917",

language = "English",

volume = "21",

pages = "7961--7964",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "19",

}

TY - JOUR

T1 - One-Pot Anodic Conversion of Symmetrical Bisamides of Ethylene Diamine to Unsymmetrical gem-Bisamides of Methylene Diamine

AU - Golub, Tatiana

AU - Dou, Gui Yuan

AU - Zeng, Cheng Chu

AU - Becker, James Y.

PY - 2019/10/4

Y1 - 2019/10/4

N2 - Symmetrical bisamides of ethylene diamine of type ArCONHCH2CH2NHCOAr undergo anodic C-C bond cleavage in acetonitrile-LiClO4 under controlled-potential electrolysis. The electrogenerated carbocation intermediates react with the solvent acetonitrile to afford unsymmetrical gem-bisamides of type ArCONHCH2NHCOMe in a one-pot reaction. The yields of the latter products are moderate (up to 60%). Other minor products involve two symmetrical gem-bisamides of type ArCONHCH2NHCOAr and MeCONHCH2NHCOMe and fragmentation products (e.g., ArCONHCHO, ArCONH2, and ArCN).

AB - Symmetrical bisamides of ethylene diamine of type ArCONHCH2CH2NHCOAr undergo anodic C-C bond cleavage in acetonitrile-LiClO4 under controlled-potential electrolysis. The electrogenerated carbocation intermediates react with the solvent acetonitrile to afford unsymmetrical gem-bisamides of type ArCONHCH2NHCOMe in a one-pot reaction. The yields of the latter products are moderate (up to 60%). Other minor products involve two symmetrical gem-bisamides of type ArCONHCH2NHCOAr and MeCONHCH2NHCOMe and fragmentation products (e.g., ArCONHCHO, ArCONH2, and ArCN).

UR - http://www.scopus.com/inward/record.url?scp=85072945249&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.9b02917

DO - 10.1021/acs.orglett.9b02917

M3 - Article

AN - SCOPUS:85072945249

SN - 1523-7060

VL - 21

SP - 7961

EP - 7964

JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

One-Pot Anodic Conversion of Symmetrical Bisamides of Ethylene Diamine to Unsymmetrical gem-Bisamides of Methylene Diamine

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this