Electrochemical Formation of Methoxy- and Cyano(phenylazo)alkanes from Aldehyde and Ketone Phenylhydrazones

Mitsuhiro Okimoto; Yukio Takahashi; Toyoji Kakuchi

doi:10.1055/s-2003-41048

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2003(13): 2057-2063
DOI: 10.1055/s-2003-41048

PAPER

Electrochemical Formation of Methoxy- and Cyano(phenylazo)alkanes from Aldehyde and Ketone Phenylhydrazones

Mitsuhiro Okimoto*^a, Yukio Takahashi^a, Toyoji Kakuchi^b
^a Department of Applied Chemistry and Circumstance Engineering, Kitami Institute of Technology, Koen-cyo165 Kitami 090-8507, Japan
Fax: +81(157)247719; e-Mail: oki@chem.kitami-it.ac.jp;
^b Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, W8N13 Kita-Ku, Sapporo 060-8628, Japan

Further Information

Publication History

Received 1 April 2003
Publication Date:
28 August 2003 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

Several aldehyde and ketone phenylhydrazones were electrooxidized in MeOH. Electrooxidation in the presence of KI or tetraethylammonium p-toluenesulfonate as the supporting electrolyte afforded the corresponding methoxy(phenylazo)alkanes, whereas electrooxidation in the presence of KI, NaCN, and HOAc afforded the cyano(phenylazo)alkanes.

Key words

electrochemical oxidations - azo compounds - hydrazones - iodide ion - electron-transfer

References

1 Schantl J. Tetrahedron Lett. 1970, 3785

Crossref Google Scholar
2 Chiusoli GP. Venturello C. Organometal. Chem. Synth. 1971, 1: 203

Google Scholar
3 Harrison MJ. Norman ROC. Gladstone WAF. J. Chem. Soc. C 1967, 735

Crossref Google Scholar
4 Iffland DC. Salisbury L. Schafer WR. J. Am. Chem. Soc. 1961, 83: 747

Crossref Google Scholar
5 Okimoto M. Chiba T. J. Org. Chem. 1990, 55: 1070

Crossref Google Scholar
6 Okimoto M. Takahashi Y. Bull. Chem. Soc. Jpn. 2002, 75: 2059

Crossref Google Scholar
7a Torii S. Electroorganic Synthesis Kodansha; Tokyo: 1985. Part 1. p.184

Crossref Google Scholar
7b Gunic E. Tabakovic I. J. Org. Chem. 1988, 53: 5081

Crossref Google Scholar
7c Tabakovic I. Trkovnik M. Galijas D. J. Electroanal. Chem. 1978, 86: 241

Crossref Google Scholar
7d Hammerich O. Parker VD. J. Chem. Soc., Perkin Trans. 1 1975, 61

Crossref Google Scholar
7e Cauquis G. Genies M. Tetrahedron Lett. 1970, 2903

Crossref Google Scholar
7f Cauquis G. Genies M. Tetrahedron Lett. 1970, 3403

Crossref Google Scholar
8a Chiba T. Okimoto M. Nagai H. Takata Y. J. Org. Chem. 1983, 48: 2968

Google Scholar
8b Chiba T. Okimoto M. Synthesis 1990, 209

Google Scholar
8c Chiba T. Okimoto M. J. Org. Chem. 1991, 56: 6163

Google Scholar
8d Chiba T. Okimoto M. J. Org. Chem. 1992, 57: 1375

Google Scholar
8e Okimoto M. Takahashi Y. Bull. Chem. Soc. Jpn 2003, 76: 1477

Google Scholar
9 Sandler SR. Karo W. Organic Functional Group Preparations Vol. 2: Academic Press; New York: 1971. p.324

Google Scholar
10a Yao HC. Resnick P. J. Org. Chem. 1965, 30: 2832

Crossref Google Scholar
10b Sandler SR. Karo W. Organic Functional Group Preparations Vol. 1: Academic Press; New York: 1968. p.379

Crossref Google Scholar
11 Chernova AV. Shagidullin RR. Kitaev YP. Zh. Org. Khim. 1967, 3: 916 ; Chem. Abstr. 1967, 67, 53349

Google Scholar