119015-52-0Relevant articles and documents
Difunctionalization of Alkenes Using 1-Chloro-1,2-benziodoxol-3-(1H)-one
Egami, Hiromichi,Yoneda, Takahiro,Uku, Minako,Ide, Takafumi,Kawato, Yuji,Hamashima, Yoshitaka
supporting information, p. 4020 - 4030 (2016/06/09)
Difunctionalization of alkenes with 1-chloro-1,2-benziodoxol-3-(1H)-one (1) was investigated. Various additional nucleophiles were tested, and oxychlorination, dichlorination, azidochlorination, chlorothiocyanation, and iodoesterfication were demonstrated. The oxychlorination product was obtained efficiently when the reaction was operated in water. Dichlorination occurred in the presence of a Lewis basic promoter, such as 4-phenylpyridine N-oxide, as an additive. The reaction with in situ-generated azido anion afforded azidochlorinated compounds with a chlorine atom at the terminal position, while the reaction with trimethylsilyl isothiocyanate produced chlorothiocyanation adducts with a chlorine atom at the benzylic position. On the other hand, when 1 was treated with tetra-n-butylammonium iodide prior to the addition of alkenes, only iodoesterification occurred selectively. These mild reactions enable convenient site-selective difunctionalizations of substrates having two alkene moieties. NMR experiments suggested that the electrophilic reactive species in each reaction varied depending on the nature of the added nucleophile.
THE REACTION OF BENZYLIC ALCOHOLS WITH CHLOROTRIMETHYLSILANE/DIMETHYL SULPHOXIDE
Bellesia, Franco,Ghelfi, Franco,Pagnoni, Ugo Maria,Pinetti, Adriano
, p. 437 - 439 (2007/10/02)
With catalytic amounts of chlorotrimethylsilane/dimethyl sulphoxide (CTMSO/DMSO) in acetonitrile benzylic alcohols have been found to give high yields of styrenes.By using stoicheiometric amounts of reagents, different reaction pathways are observed: an elimination-addition sequence occurs with secondary and tertiary alcohols affording vicinal dichloro derivatives, β-chloro thioethers and allyl chlorides, whereas a nucleophilic substitution to the corresponding monochlorides occurs starting from primary and sterically hindered substrates.