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Chemical compound
isomeric parent heterocycles are 1,2-dithiane, 1,3-dithiane and 1,4-dithiane. They are all colorless solids. 1,2-Dithiane is an organosulfur compound with
Dithiane
Chemical process intended to reverse the polarity of a molecular functional group
is converted into a dithiane or a thioacetal. In synthon terminology the ordinary carbonyl group is an acyl cation and the dithiane is a masked acyl anion
Umpolung
Chemical reaction
for acylation by converting aldehydes into lithiated 1,3-dithianes. The lithiated 1,3-dithianes serves as an acyl anion equivalent, undergoing alkylation
Corey–Seebach_reaction
Chemical compound
reversible formation of dithianes. A prototypical reaction is its formation of 1,3-dithiane from formaldehyde. The reactivity of this dithiane illustrates the
Propane-1,3-dithiol
American chemist (born 1928)
The formations of dithianes can be accomplished with a Lewis acid (scheme 7) or directly from carbonyl compounds. The pKa of dithianes is approximately
Elias_James_Corey
Chemical compound
Cyclobutanone can also be prepared in a two step procedure by dialkylation of 1,3-dithiane with 1-bromo-3-chloropropane followed by deprotection to the ketone with
Cyclobutanone
Broad-spectrum poisoning
chemically. Therefore, a prodrug, sulfanegen sodium (2,5-dihydroxy-1,4-dithiane-2,5-dicarboxylic acid disodium salt), which hydrolyzes into 2 molecules
Cyanide_poisoning
Molecule with one or more rings composed of different elements
Oxygen + Sulfur Oxathiane Oxathiin 2 × Oxygen Dioxane Dioxin 2 × Sulfur Dithiane Dithiin Nitrogen + Boron Azaborinane Azaborine Six-membered rings with
Heterocyclic_compound
Organosulfur compounds of the form –CH(O–)S– or –CH(S–)2
referred to as umpolung. The reaction is commonly performed using the 1,3-dithiane. The lithiated intermediate can be used for various nucleophilic bond-forming
Thioacetal
Chemical compound
acetylenes (H−CC−R), methyl sulfides (H−CH2SR), thioacetals (H−CH(SR)2, e.g. dithiane), methylphosphines (H−CH2PR2), furans, thiophenes and ferrocene (Fe(H−C5H4)(C5H5))
N-Butyllithium
Chemical compound
five-membered rings with the formula (CH2)3O2. 1,2-Dioxane 1,4-Dioxane Dithiane Surprenant, Kenneth S. (2000). "Dioxane". Ullmann's Encyclopedia of Industrial
1,3-Dioxane
Toxic mercury compound known as 'corrosive sublimate'
amalgamated using mercuric chloride. Mercuric chloride is used to remove dithiane groups attached to a carbonyl in an umpolung reaction. This reaction exploits
Mercury(II)_chloride
Chemical compound
Schwartz JA (March 1978). "Synthetic studies on lignan lactones: aryl dithiane route to (.+-.)-podorhizol and (.+-.)-isopodophyllotoxone and approaches
Podophyllotoxin
Chemical compound
6-hexamethyl-1,2,4-trithiane and 4-mercapto-2,2,4,6,6-pentamethyl-1,3-dithiane. The product can also be obtained by pyrolysis of allyl isopropyl sulfide
Trithioacetone
Chemical compound
carbonyl group is protected with 1,3-propanedithiol 2, producing a dithiane 3. The dithiane is deprotonated using n-Butyllithium in tetrahydrofuran, and alkylated
2,5-Undecanedione
Class of chemical compounds
(typically trimethylsilyl chloride, tmsCl). Silylation of 2-lithio-1,3-dithiane, followed by hydrolysis of the dithioacetal group with mercury(II) chloride
Acylsilane
Organic ion with a negatively charged carbon atom
Benzene C6H6 ~49 Propene C3H6 ~44 Toluene C6H5CH3 ~43 Ammonia (N–H) NH3 ~41 Dithiane C4H8S2 ~39 Dimethyl sulfoxide (CH3)2SO 35.1 Diphenylmethane C13H12 32.3
Carbanion
Chemical group (R–C=O)
chemists have developed various acyl anion synthetic equivalents, such as dithianes, as surrogates. However, as a partial exception, hindered dialkylformamides
Acyl_group
Organic reaction
Gewald reaction a 3-acetyl-2-aminothiophene is synthesized starting from a dithiane (an adduct of sulfur and acetone if R = CH3 or acetaldehyde if R = H) and
Gewald_reaction
Multienzyme complex
decarboxylation to produce an acyl anion equivalent (see cyanohydrin or aldehyde-dithiane umpolung chemistry, as well as benzoin condensation). This anion attacks
Pyruvate dehydrogenase complex
Pyruvate_dehydrogenase_complex
Chemical compound
heating with potassium hydrogen sulfate. These reactions also form 1,4-dithiane as a byproduct. The original 1912 preparation of 1,4-oxathiane involved
1,4-Oxathiane
Chemical compound
dihalides gives 1,3-dithiepanes. Oxidation gives the cyclic disulfide 1,2-dithiane: HSCH2CH2CH2CH2SH + O → S2(CH2)4 + H2O It forms self-assembled monolayers
1,4-Butanedithiol
Transmission of electronic effects through a system of conjugated chemical bonds
Fragmentation of Vinylogous Acyl Triflates: 2-Methyl-2-(1-Oxo-5-Heptynyl)-1,3-Dithiane". Organic Syntheses. 88: 353. doi:10.15227/orgsyn.088.0353. The Vinylogous
Vinylogy
Chemical compound
(1992). "Synthesis and Biological Activity of 1,2-Dithiolanes and 1,2-Dithianes Bearing a Nitrogen-containing Substituent". Bioscience, Biotechnology
Nereistoxin
Chemical compound C2H4(SH)2
and 1,3-dithiols give related 1,3-dithiolanes (five-membered) and 1,3-dithianes (six-membered rings). Diols such as ethylene glycol undergo analogous
Ethane-1,2-dithiol
Organic compounds that contain sulfur
thiiranes, thiirenes, thietanes, thietes, dithietanes, thiolanes, thianes, dithianes, thiepanes, thiepines, thiazoles, isothiazoles, and thiophenes, among
Organosulfur_chemistry
Chemical compound
1002/14356007.a26_767. ISBN 978-3-527-30673-2. "1,3-Dithiolanes, 1,3-Dithianes". Organic Chemistry Portal. Archived from the original on 17 May 2008
2-Mercaptoethanol
Unstable oxoacid of sulfur
sulfinate. Hydrogen sulfoxylate reacts with divinyl sulfone to make 1,4-dithiane 1,1,4,4-tetroxide. Perfluorophenyl iodide is reduced to pentafluorobenzene
Sulfoxylic_acid
Affect on molecular properties due to spatial arrangement of electron orbitals
a much-amplified difference in the two stereoelectronic effects in 1,3-dithiane (σ(C–H) → σ*(C–S)) than in 1,3-dioxane(σ(C–H) → σ*(C–O)). The differences
Stereoelectronic_effect
Species of flowering plant
males. Substantial amounts of thiarubrines, antifungal and nematocidal dithianes, were found in roots of plants growing throughout chimpanzee habitats
Aspilia_mossambicensis
Chemical compound
Sulfanegen Names IUPAC name 2,5-Dihydroxy-1,4-dithiane-2,5-dicarboxylic acid Identifiers CAS Number 80003-64-1 (Na+ salt) Y 1309654-46-3 3D model (JSmol)
Sulfanegen
Chemical compound found in some lichens
groups through O-benzylation and converted the benzyl ketone to a 1,3-dithiane. The synthesis utilised 2,4-dibenzyloxy-6-[(2'-pentyl-1',3'-dithian-2'-yl)methyl]benzoic
Olivetoric_acid
German chemist (born 1937)
E. J. (1975). "Generation and synthetic applications of 2-lithio-1,3-dithianes". Journal of Organic Chemistry. 40 (2): 231–237. doi:10.1021/jo00890a018
Dieter_Seebach
British chemist
California, Irvine University of York Thesis The application of [beta-keto dithianes in natural product synthesis] (2005) Doctoral advisor Steven V. Ley
Helen_Sneddon
Chemical reaction
lowered drastically when the cyclopropane ring contained a dithiane group. Even though the dithiane-substituted vinylcyclopropane substrates required two synthetic
Vinylcyclopropane rearrangement
Vinylcyclopropane_rearrangement
Chemical compound
Suriclone (Suril) is a sedative and anxiolytic drug in the cyclopyrrolone family of drugs. Other cyclopyrrolone drugs include zopiclone and pagoclone.
Suriclone
Chemical compound
dithiocarboxylate: RCLiS2C2H4 → RCS2Li + C2H4 In contrast, 2-lithio-1,3-dithianes (RCLiS2C3H6) are long-lived. 1,3-Dithiolanes are susceptible to a variety
1,3-Dithiolane
Group of atoms introduced into a compound to prevent subsequent reactions
acetals is easier than of cyclic acetals. Acylals – Removed by Lewis acids. Dithianes – Removed by metal salts or oxidizing agents. The most important protecting
Protecting_group
Chemical compound
(C5H5)2Ti. Ketones and aldehydes condense to give the heterocycles called dithianes: C6H4(SH)2 + RR’CO → C6H4(S)2CRR’ + H2O 3,4-Toluenedithiol, also called
Benzene-1,2-dithiol
Chemical compound
introducing acetic acid or substitution reactions with tosylates. Next, a dithiane derived anion interacts to form an alcohol. The following step involves
Debromoaplysiatoxin
Chemical compound
the synthesis of fragment C was the addition of the anion derived from dithiane to benzyl glycidyl ether. Palladium(0)-mediated crosscoupling of vinyl
Discodermolide
Organosulfur compound with two –SH groups
It is employed as a reagent in organic chemistry, since it forms 1,3-dithianes upon treatment with ketones and aldehydes. When derived from aldehydes
Dithiol
Drug
Suproclone is a sedative and anxiolytic drug in the cyclopyrrolone family of drugs, developed by the French pharmaceutical company Rhône-Poulenc. Other
Suproclone
α-Amino Aldehydes from Sulfinimine (N-Sulfinyl Imine)-Derived α-Amino 1,3-Dithianes. Formal Synthesis of (-)-2,3-trans-3,4-cis-Dihydroxy Proline". Tetrahedron
N-Sulfinyl_imine
Chemical compound
4-Dimethoxyphenyl)-2-(3-{[2-(3,4-dimethoxyphenyl)ethyl]methylamino}propyl)-1λ6,3λ6-dithiane-1,1,3,3-tetrone CAS Number 57010-31-8 Y PubChem CID 42107 ChemSpider 38399 N
Tiapamil
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DITHIANE
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