Ramberg-Backlund rearrangement vs. β-elimination of haloform from trichloro and trifluoromethyl sulfones

被引：13
作者：
Braverman, S [1 ]
Zafrani, Y [1 ]
机构：
[1] Bar Ilan Univ, Dept Chem, IL-52900 Ramat Gan, Israel
来源：
TETRAHEDRON | 1998年 / 54卷 / 09期
关键词：
D O I：
10.1016/S0040-4020(97)10404-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new and convenient method for the preparation of trichloro and trifluoromethanesulfinates is described. These esters readily undergo rearrangement to the corresponding sulfones at room temperature, in high yields. In contrast to trichloromethyl sulfoxides which undergo base-induced beta-elimination of chloroform to sulfines, the corresponding sulfones undergo an unusually facile Ramberg-Backlund rearrangement with formation of dichloromethylene products. Replacement of CCl3 by CF3 results in complete loss of reactivity, even under drastic basic conditions. (C) 1998 Elsevier Science Ltd. All rights reserved.
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页码：1901 / 1912
页数：12
相关论文
共 28 条
[1]  
ANDREADES S, 1964, J AM CHEM SOC, V86, P2008
[2]   RAMBERG-BACKLUND REACTION OF BENZYL ALPHA-HALOBENZYL AND HALOMETHYL SULFONES [J].
BORDWELL, FG ;
WILLIAMS, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (02) :435-&
[3]   REARRANGEMENT OF BENZYLIC TRICHLOROMETHANE-SULFONATES TO SULFOXIDES AND CHLORIDES [J].
BRAVERMA.S ;
SREDNI, B .
TETRAHEDRON, 1974, 30 (15) :2379-2384
[4]   SYNTHESIS AND REACTIVITY OF ALLYLIC AND PROPARGYLIC TRICHLOROMETHANESULFINATES [J].
BRAVERMAN, S ;
GRINSTEIN, D ;
LIOR, Z .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1993, 74 (1-4) :443-444
[5]   HIGHLY REACTIVE SULFINATES - THE SYNTHESIS, SOLVOLYSIS AND REARRANGEMENT OF BENZYL TRICHLOROMETHANESULFINATES [J].
BRAVERMAN, S ;
DUAR, Y .
TETRAHEDRON, 1990, 46 (08) :2975-2990
[6]   THE SYNTHESIS, SOLVOLYSIS AND REARRANGEMENT OF BENZYL TRIFLUOROMETHANESULFINATES [J].
BRAVERMAN, S ;
MANOR, H .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1990, 53 (1-4) :357-365
[7]   A NOVEL SYNTHESIS OF MONOSUBSTITUTED SULFINES VIA AN UNUSUAL BETA-ELIMINATION OF CHLOROFORM FROM ALLYLIC AND BENZYLIC TRICHLOROMETHYL SULFOXIDES [J].
BRAVERMAN, S ;
GRINSTEIN, D ;
GOTTLIEB, HE .
TETRAHEDRON LETTERS, 1994, 35 (06) :953-956
[8]  
BRAVERMAN S, IN PRESS TETRAHEDRON
[9]  
BRAVERMAN S, 1988, CHEM SULFONES SULFOX, pCH13
[10]   Direct conversion of dipropargylic sulfones into (E)- and (Z)-hex-3-ene-1,5-diynes by a modified one-flask Ramberg-Backlund reaction [J].
Cao, XP ;
Chan, TL ;
Chow, HF .
TETRAHEDRON LETTERS, 1996, 37 (07) :1049-1052
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