Synthesis and acetyl a study on and hydrolysis of p-toluoyl 9-triptycyl diselenides:: Generation of triptycene-9-selenenoselenoic acid

被引：9

作者：

Ishii, A ^{[1
]}

Mori, Y ^{[1
]}

Uchiumi, R ^{[1
]}

机构：

[1] Saitama Univ, Fac Sci, Dept Chem, Sakura Ku, Urawa, Saitama 3388570, Japan

来源：

HETEROATOM CHEMISTRY | 2005年 / 16卷 / 06期

关键词：

D O I：

10.1002/hc.20155

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

p-Toluoyl 9-triptycyl diselenide (9) was prepared by reaction of Se-9-triptycyl triptycene-9-selenoseleninate (7) with p-toluenecarboselenoic acid (8) and by reaction of triptycene-9-selenenoselenolate salt with p-toluoyl chloride. Acetyl 9-triptycyl diselenide (13) was prepared by reaction of triptycene-9selenenoselenolate salt with acetyl chloride. Hydrolysis of the two diselenides, 9 and 13, provided triptycene-9-selenol (10) and di-9-triptycyl triselenide (12), suggesting the generation of triptycene-9-selenenoselenoic acid (3). (c) 2005 Wiley Periodicals, Inc.

引用

页码：525 / 528

页数：4

共 21 条

[1] Nucleophilic attack at selenium in diselenides and selenosulfides. A computational study [J].

Bachrach, SM ;

Demoin, DW ;

Luk, M ;

Miller, JV .

JOURNAL OF PHYSICAL CHEMISTRY A, 2004, 108 (18) :4040-4046

[2] THIOL/DISELENIDE EXCHANGE FOR THE GENERATION OF BENZENESELENOLATE ION - CATALYTIC REDUCTIVE RING-OPENING OF ALPHA,BETA-EPOXY KETONES [J].

ENGMAN, L ;

STERN, D .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) :5179-5183

[3]

FREEMAN F, 1994, SYNTHESIS-STUTTGART, P699

[4]

GANTHER HE, 1975, CHEM SCRIPTA, VA 8, P79

[5] The first direct oxidative conversion of a selenol to a stable selenenic acid: Experimental demonstration of three processes included in the catalytic cycle of glutathione peroxidase [J].

Goto, K ;

Nagahama, M ;

Mizushima, T ;

Shimada, K ;

Kawashima, T ;

Okazaki, R .

ORGANIC LETTERS, 2001, 3 (22) :3569-3572

[6]

Goto K, 1997, LIEBIGS ANN-RECL, P2393

[7]

ISHIHARA H, 1989, SYNTHESIS-STUTTGART, P929

[8]

ISHIHARA H, 1987, SYNTHESIS-STUTTGART, P371

[9] First synthesis and characterization of isolable thioselenenic acid, triptycene-9-thioselenenic acid [J].

Ishii, A ;

Takahashi, T ;

Tawata, A ;

Furukawa, A ;

Oshida, H ;

Nakayama, J .

CHEMICAL COMMUNICATIONS, 2002, (23) :2810-2811

[10] Hydrolysis of an isolable selenoseleninate under acidic and alkaline conditions [J].

Ishii, A ;

Takahashi, T ;

Nakayama, J .

HETEROATOM CHEMISTRY, 2001, 12 (04) :198-203

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