107909-16-0Relevant articles and documents
PALLADIUM-CATALYZED COUPLING OF ELECTROGENERATED ALLYLTIN REAGENTS
Yoshida, Jun-ichi,Funahashi, Hirokatsu,Iwasaki, Hiroya,Kawabata, Nariyoshi
, p. 4469 - 4472 (1986)
Palladium-catalyzed homocoupling of allylic halides and acetates under in situ electrochemical generation of the allyltin reagent was developed.
Reaction of 1-Aryl-3-chloropropenes with Grignard Reagents. Nucleophilic Substitution versus Single-electron Transfer
Muraoka, Kiyoshige,Nojima, Masatomo,Kusabayashi, Shigekazu,Nagase, Shigeru
, p. 761 - 768 (2007/10/02)
The reactions of ambident 1-aryl-3-chloropropenes (1a-e) with a series of Grignard reagents, R'MgY (R' = Me, Pr, Ph, Pri, But; Y = Br, I), were carried out in diethyl ether (EE) and tetrahydrofuran (THF).The products were a mixture of two alkylation products (2) and (3), and three dimerization products (4)-(6).The alkylation:dimerization ratio and the composition of the two alkylation products were a marked function of substituent electronic effects in the chlorides (1a-e), R' or Y of R'MgY, and solvent.On the basis of the stereochemistry of alkylation, cyclizable probe experiments, and the effect of the addition of FeCl3 on product composition, the following conclusions were obtained.First, dimers (4)-(6) are most likely to be produced by a mechanism involving single-electron transfer (SET).Second, for the formation of alkylation products (2) and (3), three alternative pathways contribute depending on the nature of R'MgY and solvent, (a) competitive SN2-SN2' pathways in the reaction of R'MgBr in EE, (b) a process involving SET in the reaction with R'MgI in EE, and (c) SN2 pathways in the reaction of R'MgBr in THF.
