16775-67-0Relevant articles and documents
Alicyclic ring structure: Conformational influence of the CF2 group in cyclododecanes
Skibinski, MacIej,Wang, Yi,Slawin, Alexandra M. Z.,Lebl, Tomas,Kirsch, Peer,O'Hagan, David
, p. 10581 - 10584 (2011)
Getting out of the way: In fluorinated cyclododecane structures the CF 2 group locates only at corner positions (see picture). This relaxes 1,4-H,H transannular interactions as a result of C-CF2-C angle widening. Misplaced CF2 groups lead to significant ring distortion. It follows that strategic incorporation of CF2 groups has potential as a design feature to introduce order and polarity into organic hydrocarbon structures. Copyright
Low temperature syntheses of thioketals from enol ethers and carbonyl compounds
Martel, Arnaud,Chewchanwuttiwong, Sopa,Dujardin, Gilles,Brown, Eric
, p. 1491 - 1494 (2003)
A dithioacetalisation procedure at low temperature using TMSOTf as the promoter is described. This method proved highly efficient for unprecedented transprotection of ketone enol ethers and was successfully applied to polyfunctional sensitive substrates.
gem-Difluorination vs 1,3-Dithiolane-Dihydro-1,4-dithiin Rearrangement. The Role of Benzylic Carbons
Jekoe, Jozsef,Timar, Tibor,Jaszberenyi, Joseph Cs.
, p. 6748 - 6751 (1991)
1,3-Dithiolanes bearing a phenyl or substituted aromatic group and a methyl (or methylene) group attached to C-2 cannot be gem-difluorinated with 1,3-dibromo-5,5-dimethylhydantoin (DBH) (or NBS) + HF/pyridine because a rapid 1,3-dithiolane-dihydro-1,4-dit
Selective Transdithioacetalization of Acetals, Ketals, Oxathioacetals and Oxathioketals Catalyzed by Envirocat EPZ10 R
Gajare,Shingare,Bandgar
, p. 452 - 453 (1998)
Envirocat EPZ10R has been found to be a remarkable reusable heterogeneous catalyst for selective transdithioacetalization of acetals, ketals, oxathioacetals and oxathioketals with HSCH2CH2SH and HSCH2CH2/s
Silica-supported perchloric acid (HClO4-SiO2): A versatile catalyst for tetrahydropyranylation, oxathioacetalization and thioacetalization
Khan, Abu T.,Parvin, Tasneem,Choudhury, Lokman H.
, p. 2497 - 2502 (2008/02/03)
A simple and convenient synthetic protocol for the protection of hydroxyl group as tetrahydropyranyl ether as well as carbonyl functionality as oxathioacetal and thioacetal has been achieved using a catalytic amount of silica-supported perchloric acid und
A simple and efficient heterogeneous procedure for thioacetalization of aldehydes and ketones
Ali, Mohammed Hashmat,Gomes, Maria Goretti
, p. 1326 - 1332 (2007/10/03)
A new procedure for the protection of aldehydes and ketones as thioacetals promoted by catalytic amount of p-toluene-sulfonic acid and silica gel has been developed. This procedure offers versatility, short reaction time, excellent yield, good selectivity
A simple and practical synthetic protocol for acetalisation, thioacetalisation and transthioacetalisation of carbonyl compounds under solvent-free conditions
Khan, Abu T.,Mondal, Ejabul,Ghosh, Subrata,Islam, Samimul
, p. 2002 - 2009 (2007/10/03)
A wide variety of carbonyl compounds can be converted smoothly to the corresponding acetals on treatment with alcohols or diols and triethyl orthoformate in the presence of a catalytic amount of (bromodimethyl)sulfonium bromide at room temperature. Similarly, various carbonyl compounds can be transformed into the corresponding dithioacetals on reaction with thiol or dithiols at room temperature by employing the same catalyst without any solvent. Moreover, O,O-acetals can also be converted into the corresponding dithioacetals under identical conditions. Some of the major advantages are mild reaction conditions, a high degree of efficiency, compatibilty with other protecting groups and the lack of solvents, particularly for thioacetalisation. In addition, no brominations occur at the double bond or α to the keto position or even in the aromatic ring under these experimental conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
2,4,4,6-Tetrabromo-2,5-cyclohexadienone (TABCO), N-bromosuccinimide (NBS) and bromine as efficient catalysts for dithioacetalization and oxathioacetalization of carbonyl compounds and transdithioacetalization reactions
Iranpoor, Nasser,Firouzabadi, Habib,Shaterian, Hamid Reza,Zolfigol
, p. 1047 - 1071 (2007/10/03)
The use of 2,4,4,6-tetrabromo-2,5-cyclohexadienone (TABCO), N-bromosuccinimide (NBS), and bromine as efficient catalysts for conversion of carbonyl compounds to their cyclic and acyclic dithioacetals and 1,3-oxathiolanes under mild reaction conditions are described. These catalysts are also used for efficient transdithioacetalization of acetals, diacetals, ketals, acylals, enamines, hydrazones, and oximes with high yields in the presence of thiols.
gem-Difluoro Compounds: A Convenient Preparation from Ketones and Aldehydes by Halogen Fluoride Treatment of 1,3-Dithiolanes
Sondej, Susan C.,Katzenellenbogen, John A.
, p. 3508 - 3513 (2007/10/02)
gem-Difluoro compounds can be prepared from ketones and aldehydes by formation of the corresponding 1,3-dithiolanes, followed by reaction with 1,3-dibromo-5,5-dimethylhydantoin and pyridinium poly(hydrogenfluoride) (HF-pyridine) in methylene chloride.The
