90083-21-9Relevant academic research and scientific papers
Syntheses of diarylethenes by perylene-catalyzed photodesulfonylation from ethenyl sulfones
Adachi, Kazumasa,Dakegata, Aki,Fukuyama, Takahide,Okuda, Yasuhiro,Orita, Akihiro,Ryu, Ilhyong,Takemoto, Mai,Wakamatsu, Kan,Watanabe, Hikaru
supporting information, p. 409 - 412 (2020/04/27)
Diarylethenes were obtained from the corresponding ethenyl sulfones by photocatalyzed desulfonylation using UV or blue LEDs. When perylene and i-Pr2NEt were used as a photocatalyst and a sacrificing reagent, respectively, this desulfonylation proceeded smoothly to afford the desired ethenes with the functional groups such as chloro, alkoxy and heteroaromatic rings remaining untouched. The use of a flow photoreactor enabled this desulfonylation to proceed more rapidly to finish in an hour of residence time.
Integrated Chemical Process: One-Pot Double Elimination Method for Acetylenes
Orita, Akihiro,Yoshioka, Naonori,Struwe, Petra,Braier, Arnold,Beckmann, Anke,Otera, Junzo
, p. 1355 - 1363 (2007/10/03)
A novel one-pot process for synthesis of acetylenes has been achieved in which the following series of steps are integrated: addition of an α-anion of sulfone to aldehyde; trapping of the resulting adduct to incorporate a leaving group, and double elimination of this intermediate. Consolidation of Peterson elimination renders the process much simpler. This method provides a convenient and high-yielding access to a variety of enynes and polyynes as well as to functionally substituted aryl acetylenes containing halogen(s) or acetal groups, which are useful building blocks for aryl acetylene scaffolds. Iteration of the one-pot generation of acetylenic bonds provides a new metodology for the buildup of aryl acetylene skeletons.
Mechanistic Aspects and Profiles of the Double Elimination Reaction of β-Substituted Sulfones
Otera, Junzo,Misawa, Hiromitsu,Sugimoto, Kiyoto
, p. 3830 - 3833 (2007/10/02)
The double elimination reaction of β-acetoxy or β-alkoxy sulfones was investigated in detail by employing some representative reactions.Successful isolation of reaction intermediates revealed the reaction path: the first step is elimination of the acetoxy group to afford a vinyl sulfone.The subsequent elimination of a phenylsulfonyl group from the vinyl sulfone gives acetylenes, while polyenes are formed in cases where isomerization of the vinyl sulfone to an allyl sulfone is possible prior to the second elimination.Besides these mechanistic considerations, general features are discussed in order to make clear the scope and limitations of this synthetically useful reaction.
