20343-90-2Relevant articles and documents
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 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.
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.
