54576-37-3Relevant articles and documents
Iterative stereospecific reagent-controlled homologation of pinacol boronates by enantioenriched α-chloroalkyllithium reagents
Blakemore, Paul R.,Burge, Matthew S.
, p. 3068 - 3069 (2008/02/05)
Reaction of pinacol boronates with putative enantioenriched α-chloroalkyllithium species, generated in situ from homochiral α-chloroalkylsulfoxides by sulfoxide ligand exchange with t-BuLi in PhMe at -78 °C, gave chain-extended boronic ester products with generally excellent stereochemical fidelity. Iteration of this stereospecific reagent-controlled homologation (StReCH) process enabled the programmed synthesis of all four stereoisomers of a stereodiad-containing model system (4-benzyl-1,6-diphenylhexan-2-ol) with er ≥ 97:3 in all cases. Copyright
The reaction of (Arylthio)trimethylgermanes with various haloalkanes -Steric effect on the reaction mechanism-
Kozuka, Seizi,Nitta, Takemi
, p. 2843 - 2845 (2007/10/02)
A kinetic study has been conducted on the reactions of (arylthio) trimethylgermanes with various haloalkanes. Bimolecular nucleophilic attack of the sulfur atom has been found as the mechanisms for the reactions with normal haloalkanes while the mechanism was found to deviate from bimolecular attack to unimolecular ionization of the haloalkane, dependent on the structure of the alkyl groups with increasing of the steric hindrance. Reaction of a secondary haloalkane also proceeded by unimolecular ionization.
MODERN FRIEDEL-CRAFTS CHEMISTRY. XI. CYCLIZATION OF ARYL HALOALKYL SULFONES, ARYLSULFONYLACYL CHLORIDES AND THEIR CORRESPONDING SULFIDES
Abdel-Wahab, Aboel-Magd A.,El-Khawaga, Ahmed M.,El-Zohry, Maher F.,Khalaf, Ali A.
, p. 31 - 44 (2007/10/02)
The sulfone group deactivation for cyclialkylation and cycliacylation reactions in the presence of Friedel-Crafts catalysts was demonstrated in a number of aryl chloroalkylsulfones (1-8) and arylsulfonylacyl chlorides (17a-22a), respectively.As expected, the corresponding arylchloroalkyl sulfides (9-16) and arylmercaptoacyl chlorides (13a-28a) underwent ring-closure reaction in most cases under the same conditions.The ease of cyclization was governed by the ring size, the stability of the attacking carbocation and the nucleophilicity of the aryl moiety.Also, the behaviour of benzyl sulfones (29, 31a, and 32a) and sulfides (33, 34a and 36a) was inconsistent.Noteworthy, the Friedel-Crafts cyclization reaction is thus considered an accessible method for the synthesis of compounds 37-41 and 45, 51.