116249-82-2Relevant academic research and scientific papers
SENSITIVE NATURE OF LIGAND COUPLING AND PSEUDOROTATION TO ELECTRONIC EFFECT OF SUBSTITUENT---LIGAND COUPLING IN THE REACTIONS OF BENZYLIC ARYL SULFOXIDES WITH BENZYLIC GRIGNARD REAGENTS
Wakabayashi, Shoji,Ishida, Masahiro,Takeda, Takashi,Oae, Shigeru
, p. 4441 - 4444 (2007/10/02)
Unlike the reaction of benzylic 2-pyridyl sulfoxides with benzylic Grignard reagents, in the reaction of p-benzenesulfonylphenyl benzylic sulfoxides with benzylic Grignard reagents, benzylic groups bearing an electronwithdrawing group tends to couple with the aryl group preferentially.This change is considered to be due to a slight change of electronic environements which would effect on the ease of pseudorotation of the incipient ?-sulfurane formed during the reaction.
OCCURRENCE OF LIGAND COUPLING IN THE REACTIONS OF VARIOUS SULFOXIDES WITH GRIGNARD REAGENTS
Kawai, Tsutomu,Kodera, Yoichi,Furukawa, Naomichi,Oae, Shigeru,Ishida, Masahiro,et al.
, p. 139 - 148 (2007/10/02)
Ligand coupling reactions take place not only between benzyl and 2-pyridyl groups and two 2-pyridyl groups in the treatment of benzyl, alkyl and aryl 2-pyridyl sulfoxides with Grignard reagents, but also between such groups as p-benzenesulfonylphenyl, 4-pyridyl, 2-quinolyl and 2-pyrimidyl, and the benzyl group.There are cases in which ligand exchange precedes ligand coupling, especially with 2-heteroaryl groups.In addition, even some alkyl groups were found to couple with the 2-pyridyl group.The ease of coupling seems to be associated with the electronegativity of the coupling carbon atom of the ligand, when one compares the 13C NMR chemical shifts.
