An attractive method for producing cis-1,2-dihydroxy-3-methylcyclohexa-3,5-diene (toluene cis glycol) was developed employing a cis dihydrodiol dehydrogenase "deficient" strain of Rhodococcus (MA 7249). The toluene cis glycol produced was found to have optical rotations of [alpha]D25 = +25.8 (c 0.45, CH3OH) and +72.8 (c 0.42, CHCl3) which indicated an absolute configuration of (1S,2R) when compared with previously published values. When cultivated in laboratory fermentor in the presence of toluene vapors, MA 7249 reached a toluene cis glycol concentration up to 18 g/l in 110 h. Culture MA 7249 also accumulated cis (1S,2R) dihydrodiols from dihydronaphthalene, biphenyl, chlorobenzene, and styrene.
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J Org Chem
December 2024
Department of Chemistry, National Institute of Technology, Tiruchirappalli 620015, Tamilnadu, India.
Sodium salt of aryl sulfinic acid reacts with enynone in a different manner, yielding α-furyl sulfone and stereodefined vinyl sulfone in toluene and EtOH respectively in the presence of ZnCl. The salient features of this protocol include chemoselectivity, broad substrate scope, high efficiency, high yield, and easy purification. The synthetic utilities of the products are demonstrated by cycloaddition and cis-trans photoisomerization reactions.
View Article and Find Full Text PDFCarbohydr Res
December 2024
Department of Chemistry, School of Basic and Applied Sciences, Central University of Tamil Nadu (CUTN), Thiruvarur, 610 005, India. Electronic address:
In this report, the design and synthesis of cholesterol-based sugar azobenzene derivatives as photo-responsive organogelators have been carried out. The gel formation in different solvents was examined, and a minimum CGC of 0.5 % (w/v) was attained in toluene.
View Article and Find Full Text PDFACS Appl Mater Interfaces
October 2024
Department of Materials Science and Engineering, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, South Korea.
Upcoming regulations aim to ban per- and polyfluoroalkyl substances (PFAS), including commercial polymeric PFAS, or fluoropolymers, such as poly(tetrafluoroethylene) (PTFE) and poly(vinylidene fluoride) (PVDF), due to their environmental and toxicological impacts. However, fluoropolymers also provide crucial properties for clean energy transitions, and their regulation may hinder further technological advancements. Therefore, a facile one-pot recycling-upcycling strategy for fluoropolymers using inexpensive biomass, such as cellulose nanocrystals (CNCs), as absorbents and cocomponents for fluoro-functionalized composites could align with global sustainability goals and technological demands.
View Article and Find Full Text PDFChem Sci
August 2024
School of Science, Harbin Institute of Technology (Shenzhen) Taoyuan Street, Nanshan District Shenzhen 518055 China
A novel Ir-catalyzed asymmetric hydrogenation protocol for the synthesis of chiral tetrahydroquinoxaline (THQ) derivatives has been developed. By simply adjusting the reaction solvent, both enantiomers of mono-substituted chiral THQs could be selectively obtained in high yields with excellent enantioselectivities (toluene/dioxane: up to 93% yield and 98% ee (); EtOH: up to 83% yield and 93% ee ()). For 2,3-disubstituted chiral THQs, the -hydrogenation products were obtained with up to 95% yield, 20 : 1 dr, and 94% ee.
View Article and Find Full Text PDFChem Sci
August 2024
Department of Inorganic and Physical Chemistry, Indian Institute of Science Bangalore-560012 India
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