ANODIC CLEAVAGE OF SEVERAL KETONE N-PHENYLSEMICARBAZONES INTO METHYL N-PHENYLCARBAMATE AND THE CORRESPONDING DIMETHYL ACETALS

被引：2

作者：

Nishikawa, Shinnosuke ^{[1
]}

Yamamori, Haruki ^{[1
]}

Ohashi, Kousuke ^{[1
]}

Okimoto, Mitsuhiro ^{[1
]}

Hoshi, Masayuki ^{[1
]}

Yoshida, Takashi ^{[1
]}

机构：

[1] Kitami Inst Technol, Dept Biotechnol & Environm Chem, Koen, Hokkaido 0908507, Japan

来源：

SYNTHETIC COMMUNICATIONS | 2013年 / 43卷 / 13期

关键词：

Dimethyl acetal; electron carrier; electrooxidation; iodonium ion; ketone N-phenylsemicarbazone; methyl N-phenylcarbamate; HYPERVALENT IODINE OXIDATION; ELECTROCHEMICAL OXIDATION; ELECTROOXIDATIVE CYCLIZATION; CARBONYL-COMPOUNDS; ACYLHYDRAZONES; HYDRAZONES; CONVERSION; EFFICIENT; OXIMES; 1,3,4-OXADIAZOLES;

D O I：

10.1080/00397911.2012.667184

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several ketone N-phenylsemicarbazones were electrooxidized in the presence of potassium iodide and a base using methanol as the solvent to give nearly commensurate amounts of methyl N-phenylcarbamate and the corresponding dimethyl acetals. Continuous evolution of gaseous nitrogen was observed from the anolyte during the electrooxidation. The reactions were carried out under very mild reaction conditions and are presumed to proceed through a four-electron oxidation process, in which the iodide ion plays an important role as an electron carrier.

引用

页码：1766 / 1771

页数：6

共 21 条

[11] Electrooxidative conversion of dibenzoylbenzene dihydrazones into the corresponding bis-diazo compounds and bis-dimethyl acetals
Okimoto, M
Numata, K
Tomozawa, K
Shigemoto, T
Hoshi, M
Takahashi, Y
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 2005, 58 (07) : 560 - 563
[12] Electrochemical oxidation of benzylic amines into the corresponding imines in the presence of catalytic amounts of KI
Okimoto, M
Takahashi, Y
Numata, K
Nagata, Y
Sasaki, G
[J]. SYNTHETIC COMMUNICATIONS, 2005, 35 (15) : 1989 - 1995
[13] Electrooxidative conversion of aldehyde and ketone phenylhydrazones into the methoxy(phenylazo)alkanes
Okimoto, M
Nagata, Y
Takahashi, Y
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2003, 76 (07) : 1447 - 1448
[14] Anodic oxidation of ketone allylhydrazones into the corresponding azines
Okimoto, Mitsuhiro
Yoshida, Takashi
Hoshi, Masayuki
Hattori, Kazuyuki
Komata, Masashi
Tomozawa, Kenta
Chiba, Tomohito
[J]. SYNTHETIC COMMUNICATIONS, 2008, 38 (19) : 3320 - 3328
[15] Electrooxidative cyclization of benzylideneaminothiophenols to the corresponding 2-arylbenzothiazoles
Okimoto, Mitsuhiro
Yoshida, Takashi
Hoshi, Masayuki
Hattori, Kazuyuki
Komata, Masashi
Tomozawa, Kenta
Chiba, Tomohito
[J]. HETEROCYCLES, 2008, 75 (01) : 35 - 42
[16] Pilgram K., 2009, J HETEROCYCLIC CHEM, V13, P1257
[17] Hypervalent iodine oxidation of hydrazones of some nitrogen heterocyclic ketones and aldehydes: An efficient synthesis of fused 1,2,3-triazoloheterocycles
Prakash, O
Gujral, HK
Rani, N
Singh, SP
[J]. SYNTHETIC COMMUNICATIONS, 2000, 30 (03) : 417 - 425
[18] Refaey SAM, 2008, INT J ELECTROCHEM SC, V3, P325
[19] Shriner R.L., 1948, SYSTEMATIC IDENTIFIC, V231, P262
[20] HYPERVALENT IODINE OXIDATION OF N-ACYLHYDRAZONES AND N-PHENYLSEMICARBAZONE - AN EFFICIENT METHOD FOR THE SYNTHESIS OF DERIVATIVES OF 1,3,4-OXADIAZOLES AND DELTA(3)-1,3,4-OXADIAZOLINES
YANG, RY
DAI, LX
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (12) : 3381 - 3383

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