13702-07-3Relevant academic research and scientific papers
General synthesis of alkyl phenyl selenides from organic halides mediated by zinc in aqueous medium
Bieber, Lothar W.,De Sá, Ana C.P.F.,Menezes, Paulo H.,Gon?alves, Simone M.C.
, p. 4597 - 4599 (2007/10/03)
Organic halides of different structural types react with diphenyl diselenide and zinc dust in aqueous medium to give alkyl phenyl selenides. Benzylic and allylic bromides, α-bromoesters, acids and ketones and some primary alkyl iodides produce high yields even under acidic conditions. Less reactive halides need basic medium. The reaction proceeds equally well in the presence of various unprotected functional groups. Control experiments support a SH2 mechanism via alkyl radicals.
Study of the decomposition of halo adducts derived from propargylic phenylselenides. Intermediate formation of haloallenes
Duclos, Jean-Francois
, p. 2627 - 2630 (2007/10/02)
The decomposition of bromo- and chloro-adducts, derived from propargylic phenylselenides, leads to 1,3-dihalo 2-phenylseleno propene derivatives through intermediate formation of haloallenes.
SELECTIVE ONE-POT SYNTHESIS OF ALLENYL PHENYL SELENIDE AND 1-(PHENYLSELENO)PROPYNE. ROLE OF SODIUM BENZENESELENOLATE AS A BASE IN DMF
Saito, Seiki,Hamano, Shin-ichi,Inaba, Masami,Moriwake, Toshio
, p. 1105 - 1110 (2007/10/02)
The reaction of excess sodium benzeneselenolate with propargyl bromide in DMF-THF at room temperature produced allenyl phenyl selenide or 1-(phenylseleno)propyne selectively, depending only on the reaction time.
Selenium--Stabilized Anions. Preparation of α,β-Unsaturated Carbonyl Compounds Using Propargyl Selenides. Synthesis of (+/-)-7-Hydroxymyoporone
Reich, Hans J.,Shah, Shrenik K.,Gold Paul M.,Olson Richard E.
, p. 3112 - 3120 (2007/10/02)
The reaction of alkyl halides, carbonyl compounds, and trimethylsilyl chloride with the mono- and dianion (1) prepared by deprotonation of phenyl propargyl selenide with lithium diisopropylamide gives 1- or 3-monosubstituted or 1,3-disubstituted propargyl selenides (3a).Oxidation to selenoxides (3b) results in rearrangement to 2-(phenylseleno)-1,3-disubstituted propenones.The rate of rearrangement of propargyl selenoxides increases dramatically when the phenyl group is replaced by a 2-nitrophenyl group, and an intermediate allenyl selenate ester (7c) can be observed by low-temperature NMR.By appropriate modification of oxidation conditions, modest yields of 2-iodopropenes (e.g., 10) or the selenium-free enones or enals can be obtained.A synthesis of (+/-)-7-hydroxymyoporone (15) and its epimer has been carried out by using the dianion 1 to assemble the carbon skeleton.The preparation of α-lithioallenyl phenyl selenide (26) has been accomplished, and its reaction with electrophiles has been studied.
