SYNTHESIS OF 2-[[(PARA-NITROPHENYL)SULFONYL]OXY] 3-KETO ESTERS FROM 3-KETO ESTERS AND (PARA-NITROPHENYL)SULFONYL PEROXIDE

被引:34
作者
HOFFMAN, RV
WILSON, AL
KIM, HO
机构
[1] Department of Chemistry, New Mexico State University, Las Cruces
关键词
D O I
10.1021/jo00291a030
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The preparation of 2-[[(p-nitrophenyl)sulfonyl]oxy] /3-keto esters from /3-keto esters and (p-nitrophenyl)sulfonyl peroxide is described. High yields are obtained for a variety of structural types. One /3-diketone was also used and gave comparable success. These materials can serve as precursors to 2-nosyl ketones by decarboxylation, 3-hydroxy-2-nosyl esters by reduction, and tricarbonyl compounds by reductive elimination. © 1990, American Chemical Society. All rights reserved.
引用
收藏
页码:1267 / 1270
页数:4
相关论文
共 35 条
[2]   ARYLSULFONOXYLATION OF AROMATIC COMPOUNDS .2. PARTIAL RATE FACTORS FOR NITROPHENYLSULFONOXYLATION OF ALKYLBENZENES [J].
DANNLEY, RL ;
GAGEN, JE ;
STEWART, OJ .
JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (09) :3076-&
[3]   TRIFLUOROMETHANESULFONATES OF ALPHA-HYDROXYCARBOXYLATES - EDUCTS FOR THE RACEMIZATION - FREE SYNTHESIS OF N-SUBSTITUTED ALPHA-AMINO-ACIDS [J].
EFFENBERGER, F ;
BURKARD, U ;
WILLFAHRT, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1983, 22 (01) :65-66
[4]  
FLYNN GA, 1987, J AM CHEM SOC, V109, P7614
[5]  
GUANTI G, 1989, CHEM LETT, P1686
[6]   SYNTHESIS OF ALPHA-ARYLSULFONOXY KETONES FROM KETONE DERIVATIVES [J].
HOFFMAN, RV ;
CARR, CS ;
JANKOWSKI, BC .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) :5148-5151
[7]   REGIOSPECIFIC SYNTHESIS OF ALPHA-ARYLSULFONOXY KETONES FROM KETONE DERIVATIVES [J].
HOFFMAN, RV ;
CARR, CS .
TETRAHEDRON LETTERS, 1986, 27 (48) :5811-5812
[8]   THE REACTIONS OF ALPHA-ARYLSULFONOXY KETONES WITH NUCLEOPHILES [J].
HOFFMAN, RV ;
JANKOWSKI, BC ;
CARR, CS ;
DUESLER, EN .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (02) :130-135
[9]  
HOFFMAN RV, 1985, SYNTHESIS-STUTTGART, P760
[10]   SYNTHESIS OF 2-(((PARA-NITROPHENYL)SULFONYL)OXY) ESTERS FROM KETENE SILYL ACETALS AND BIS((PARA-NITROPHENYL)SULFONYL) PEROXIDE [J].
HOFFMAN, RV ;
KIM, HO .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (16) :3855-3857