TY - JOUR
T1 - Studies on NaI/DMSO induced retro-Michael addition (RMA) reactions on some 1,5-dicarbonyl compounds
AU - Rao, H. Surya Prakash
AU - Jothilingam, S.
PY - 2005/1
Y1 - 2005/1
N2 - Studies on the reaction of some 1,5-ketodiesters/1,5-diketones with NaX (X = Cl/Br/I)/ DMSO have shown that under microwave/thermal conditions, facile refro-Michael addition (RMA) reaction takes place instead of formation of the expected Krapcho products. Mechanistic studies have shown that the NaI/DMSO system is a better system than NaCl/DMSO or NaBr/DMSO to promote the RMA pathway and DMSO is an essential requirement. The electrophilic halide ion could be involved in this fragmentation reaction.
AB - Studies on the reaction of some 1,5-ketodiesters/1,5-diketones with NaX (X = Cl/Br/I)/ DMSO have shown that under microwave/thermal conditions, facile refro-Michael addition (RMA) reaction takes place instead of formation of the expected Krapcho products. Mechanistic studies have shown that the NaI/DMSO system is a better system than NaCl/DMSO or NaBr/DMSO to promote the RMA pathway and DMSO is an essential requirement. The electrophilic halide ion could be involved in this fragmentation reaction.
KW - Microwave-mediated organic reactions
KW - Retro reactions
KW - retro-Michael addition
UR - http://www.scopus.com/inward/record.url?scp=13444309422&partnerID=8YFLogxK
U2 - 10.1007/BF02704358
DO - 10.1007/BF02704358
M3 - Article
AN - SCOPUS:13444309422
SN - 0253-4134
VL - 117
SP - 27
EP - 32
JO - Journal of Chemical Sciences
JF - Journal of Chemical Sciences
IS - 1
ER -