Stereoselective nitration of asymmetric hydrazones with nitric oxide

被引：5

作者：

Wu, Wen-tao ^{[1
]}

Su, Gang ^{[1
]}

Lu, Zhou ^{[1
]}

Wu, Long-min ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 47期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1016/j.tetlet.2007.09.128

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nitration of asymmetric hydrazones with nitric oxide occurred stereoselectively at C1'-atom, giving mono-nitrated trans isomer as a major outcome. The ratio of trans to cis was up to >99. Higher isolated yields of nitrated products and higher trans/cis ratios of isomers suggest that this procedure offers advantages for synthesizing asymmetry nitro compounds. (C) 2007 Elsevier Ltd. All rights reserved.

引用

页码：8293 / 8296

页数：4

共 17 条

[1]

BATTETT AGM, 1986, CHEM REV, V86, P751

[2] THE REACTION OF NITRIC OXIDE WITH ISOBUTYLENE [J].

BROWN, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (10) :2480-2488

[3]

FEUER H, 2001, NITRO GROUP ORGANIC

[4]

Feuer H., 1969, CHEM NITRO NITROSO 1

[5] A new synthesis of alkyl nitrites: The reaction of alkyl alcohols with nitric oxide in organic solvents [J].

Grossi, L ;

Strazzari, S .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (22) :8076-8079

[6] A convenient method for the preparation of nitro olefins by nitration of olefins with nitrogen monoxide [J].

Hata, E ;

Yamada, T ;

Mukaiyama, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1995, 68 (12) :3629-3636

[7] The addition of nitric oxide to 1,5-dimethylhexa-2,4-diene; X-ray crystal structure determination of the major product, (E)-2,5-dimethyl-2,5-dinitrohex-3-ene [J].

Kelly, DR ;

Jones, S ;

Adigun, JO ;

Koh, KSV ;

Hibbs, DE ;

Hursthouse, MB ;

Jackson, SK .

TETRAHEDRON, 1997, 53 (50) :17221-17234

[8] Highly stereoselective nitration of chalcone derivatives with nitric oxide [J].

Li, Rui ;

Liu, Zhongquan ;

Zhou, Yulu ;

Wu, Longmin .

SYNLETT, 2006, (09) :1367-1368

[9]

MULLER E, 1992, METHODEN ORANISCHE C, V10

[10] Reactions of nitric oxide and nitrogen dioxide with functionalised alkenes and dienes [J].

Park, JSB ;

Walton, JC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1997, (12) :2579-2583

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