20343-90-2Relevant academic research and scientific papers
Synthesis, Absolute Configurations, and Biological Activities of Floral Scent Compounds from Night-Blooming Araceae
Stamm, Patrick,Etl, Florian,Maia, Artur Campos D.,D?tterl, Stefan,Schulz, Stefan
, p. 5245 - 5254 (2021)
The uncommon jasmone derivatives dehydrojasmone, isojasmol, and isojasmyl acetate, floral scent compounds from night-blooming Araceae, were synthesized in a scalable synthesis employing conjugate addition with a selenoacetal as the key step. The stereoselective strategy with subsequent enzymatic kinetic resolution allowed determining the absolute configuration of the natural compounds by GC on a chiral phase. The homoterpene (E)-4,8-dimethyl-1,3,7-nonatrien-5-yl acetate, another uncommon scent compound, was obtained by α-regioselective aldehyde prenylation. The biological activities of dehydrojasmone and isojasmol were investigated in field assays, showing that these unique volatiles are able to selectively attract specific cyclocephaline scarab beetle pollinators.
Regioselective Synthesis of Selenide Ethers through a Decarboxylative Coupling Reaction
Cui, Fei-Hu,Chen, Jing,Su, Shi-Xia,Xu, Yan-Li,Wang, Heng-Shan,Pan, Ying-Ming
, p. 3950 - 3961 (2017/11/20)
An efficient and selective approach to the synthesis of selenide ethers containing one or two geminal C–Se bonds from readily available diselenides and phenylacetic acids was developed. Compounds containing one C–Se bond were prepared by employing air as the oxidant under metal-free conditions, whereas compounds having two geminal C–Se bonds were formed via the iron(III) chloride/oxygen/cesium carbonate (FeCl3/O2/Cs2CO3) system. Moreover, 1,2-diphenyldisulfane also could be smoothly converted into the corresponding sulfur ether product under the standard reaction conditions. (Figure presented.).
Regioselective transition metal- and halogen-free direct dithiolation at C(sp3)-H of nitrotoluenes with diaryl disulfides
Kumar, Shailesh,Kadu, Rahul,Kumar, Sangit
supporting information, p. 9210 - 9214 (2016/10/13)
Here we describe a potassium tert-butoxide-mediated regioselective direct C-S bond formation at the C(sp3)-H position of nitrotoluenes with disulfides in DMSO at room temperature. The developed reaction generated, in good yields, various dithioacetals having OMe, halogen, and NH2 functionalities at various positions of the arene rings of the disulfides. Interestingly, in the absence of nitrotoluene, diaryl disulfides and diselenides underwent one-carbon homologation to form dithioacetals and diselenoacetals. Synthesized dithioacetals were transformed into 4-nitrobenzaldehyde and 7-(bis(phenylthio)methyl)-1H-indole.
Bromomethyllithium-mediated chemoselective homologation of disulfides to dithioacetals
Pace, Vittorio,Pelosi, Azzurra,Antermite, Daniele,Rosati, Ornelio,Curini, Massimo,Holzer, Wolfgang
supporting information, p. 2639 - 2642 (2016/02/18)
An efficient, chemoselective homologation of disulfides and diselenides to the corresponding dithio- and diselenoacetals has been developed via the addition of bromomethyllithium. Chemoselectivity is fully preserved in the presence of concomitant electrophilic sites decorating the substrates. The synthetic potential of selected dithioacetals has been evaluated in Feringa-Fa?anas-Mastral-type Pd-catalyzed coupling with an organolithium and in the unusual 1,4-addition to a Weinreb amide.
Ruthenium complexes of thiaporphyrin and dithiaporphyrin
Chuang, Chuan-Hung,Ou, Chen-Kuo,Liu, Shan-Tung,Kumar, Anil,Ching, Wei-Min,Chiang, Pei-Chun,Dela Rosa, Mira Anne C.,Hung, Chen-Hsiung
body text, p. 11947 - 11957 (2012/01/31)
Successful synthesis and characterization of the six-coordinated complex [Ru(STTP)(CO)Cl] (1; STTP = 5,10,15,20-tetratolyl-21-thiaporphyrinato) allowed the development of the coordination chemistry of ruthenium-thiaporphyrin through dechlorination and metathesis reactions. Accordingly, [RuII(STTP) (CO)X] (X = NO3- (2), NO2- (3), and N3- (4)) was synthesized and analyzed by single-crystal X-ray structural determination and NMR, UV-vis, and FT-IR spectroscopic methods. An independent reaction of STPPH and [Ru(COD)Cl2] led to [Ru III(STTP)Cl2] (5), which possessed a higher-valent Ru(III) center and exhibited good stability in the solution state. This stability allowed reversible redox processes in a cyclic voltammetric study. Reactions of [Ru(S2TTP)Cl2] (S2TTP = 5,10,15,20-tetratolyl- 21,23-dithiaporphyrinato) with AgNO3 and NaSePh, also via the metathesis strategy, resulted in novel dithiaporphyrin complexes [Ru II(S2TTP)(NO3)2] (6) and [Ru 0(S2TTP)(PhSeCH2SePh)2] (7), respectively. The structures of 6 and 7 were corroborated by X-ray crystallographic analyses. Complex 7 is an unprecedented ruthenium(0)- dithiaporphyrin with two bis(phenylseleno)methanes as axial ligands. A comparison of the analyses of the crude products from reactions of NaSePh and CH2Cl2 with or without [Ru(S2TTP)Cl 2], further supported by UV-vis spectral changes under stoichiometric reactions between [Ru(S2TTP)Cl2] and NaSePh, suggested a reaction sequence in the order of (1) formation of a putative [Ru II(S2TTP)(SePh)2] intermediate, followed by (2) the concerted formation of PhSe-CH2Cl and simultaneously a reduction of Ru(II) to Ru(0) and finally (3) nucleophilic substitution of PhSeCH 2Cl by excess PhSe-, resulting in PhSeCH2SePh, which readily coordinated to the Ru(0) and completed the formation of bis(phenylseleno)methane complex 7.
1-(organoselanyl)perfluoroalkanols: A stable and efficient precursor for organoselenols
Yamamoto, Terahisa,Moriura, Eri,Sawa, Arisa,Yoshimatsu, Mitsuhiro
scheme or table, p. 1046 - 1047 (2009/12/03)
The 1-(organoselanyl)perfluoroalkanols 1, 3, 4, and 10 were successfully prepared and reactions with hexanoyl chlorides to produce the corresponding esters 5, 7, and 8, accompanied by the selenoesters 6 were conducted. The DBU-mediated alkylations of the heptafluorobutanols 4, 10, and the α-p-nitro-benzoate 2 with alkyl halides easily provided alkyl phenyl selenides 9a-9i and 11a-11c in good to high yields. Copyright
Rhodium-catalyzed reductive coupling of disulfides and diselenides with alkyl halides, using hydrogen as a reducing agent
Ajiki, Kaori,Hirano, Masao,Tanaka, Ken
, p. 4193 - 4195 (2007/10/03)
(Chemical Equation Presented) We have established that RhCl(PPh 3)3 catalyzes a reductive coupling of disulfides and diselenides with alkyl halides in the presence of triethylamine using hydrogen as a reducing agent. This reaction serves as a convenient new method to produce unsymmetrical sulfides and selenides from disulfides and diselenides instead of unstable and odoriferous thiols and selenols.
The reaction of phenylselenenyl triflate with diazo compounds
Curini,Epifano,Marcotullio,Rosati
, p. 1813 - 1815 (2007/10/03)
The reaction of phenylselenenyl triflate with diazo compounds is described. Diazoalkanes, α-diazoketones and α-diazoesters gave the corresponding di(phenylselanyl) derivatives either at 0 °C or at room temperature, α-Diazo-β-dicarbonyl compounds gave selectively di(phenylselanyl) derivatives at - 78 °C, while they gave a mixture of di(phenylselanyl)- and mono(phenylselanyl) derivatives either at 0 °C or at room temperature.
A convenient synthesis of arylselenoacetals and α-halo-α-(phenylseleno)alkanes
Silveira,Perin,Braga
, p. 117 - 126 (2007/10/02)
α-Halo-α-(phenylseleno)alkanes are prepared by treatment of selenoacetals with halogenating agents. Selenoacetals are produced by heating α-halo-α-(phenylseleno)alkanes on neutral alumina
A New Method of Generation of α-Selenocarbenium Ions from Se,O-Heteroacetals and Their Reactions
Yoshimatsu, Mitsuhiro,Sato, Takashi,Shimizu, Hiroshi,Hori, Mikio,Kataoka, Tadashi
, p. 1011 - 1019 (2007/10/02)
Various Se,O-heteroacetals were prepared by the LiAlH4 reduction of diselenides 1 followed by alkylation with methoxymethyl chloride or (2-methoxyethoxy)methyl (MEM) chloride.Olefinic and acetylenic α-seleno carbenium ions were generated by the selective C-O bond cleavage of O-(2-methoxyethyl)-Se,O-heteroacetals with titanium(IV) chloride and cyclized to give the seleno heterocyclic compounds.Olefinic MEM-selenides 3a,b,d-f,h underwent the endo-mode cyclization to afford 4-chloroselenacycloalkanes 4a,b,d-f,h in good yields, whereas acetylenic MEM-selenides 12b-e,g-j underwent the exo-mode cyclization to give 3-(1-chloroalkylidene)selenacycloalkanes 13b-e,g-j.This new utilization of α-seleno carbenium ions was also applied to the intramolecular and intermolecular Friedel-Crafts reactions.
