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Akihiko Ishii - One of the best experts on this subject based on the ideXlab platform.
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practical synthesis of thiirene 1 oxides that possess two bulky alkyl substituents
Heteroatom Chemistry, 2002Co-Authors: Juzo Nakayama, Yoshiaki Sugihara, Kenta Takahashi, Michiyo Morita, Akihiko IshiiAbstract:Acetylenes that possess two bulky alkyl substituents reacted with Sulfur Dichloride to furnish the corresponding 2,3-dialkyl-2,3-dichlorothiiranes (5) nearly quantitatively. The alkaline hydrolysis of 5 afforded 2,3-dialkylthiirene 1-oxides (10) in high yields. These two reactions could be successively carried out in one flask, and 2,3-di-tert-butyl-, 2,3-di-(1-adamantyl)-, and 2-(1-adamantyl)-3-tert-butylthiirene 1-oxides (10a–c) were obtained in 70, 80, and 90% yields, respectively, based on the starting acetylenes, thus providing the most convenient synthesis of thiirene 1-oxides. DiSulfur Dichloride also reacted with acetylenes to give 5 in good yields with the elimination of one Sulfur atom. Although the alkaline hydrolysis of 5 provided 10 exclusively, acid hydrolysis gave a mixture of α-oxothioketone 9 and thiirene 1-oxide 10 in modest yields. All thiirene 1-oxides 10a–c isomerized to produce α-oxothioketones 9 in high yields when heated in boiling toluene. Reactions of a bis-acetylene (18) with diSulfur Dichloride and with Sulfur Dichloride gave a dihydropentathiepin (19) in high yields. © 2002 Wiley Periodicals, Inc. Heteroatom Chem 13:424–430, 2002; Published online in Wiley Interscience (www.interscience.wiley.com). DOI 10.1002/hc.10070
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a convenient synthesis of thiirene 1 oxides
Tetrahedron Letters, 2001Co-Authors: Juzo Nakayama, Yoshiaki Sugihara, Kenta Takahashi, Akihiko IshiiAbstract:Abstract Acetylenes ( 1 ), carrying two bulky alkyl substituents, reacted with Sulfur Dichloride (ClSCl) to give 2,3-dialkyl-2,3-dichlorothiiranes ( 2 ) nearly quantitatively. The alkaline hydrolysis of crude 2 resulted in the formation of thiirene 1-oxides ( 3 ) in 68–90% yields based on 1 , thus providing a convenient synthesis of 3 .
Juzo Nakayama - One of the best experts on this subject based on the ideXlab platform.
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practical synthesis of thiirene 1 oxides that possess two bulky alkyl substituents
Heteroatom Chemistry, 2002Co-Authors: Juzo Nakayama, Yoshiaki Sugihara, Kenta Takahashi, Michiyo Morita, Akihiko IshiiAbstract:Acetylenes that possess two bulky alkyl substituents reacted with Sulfur Dichloride to furnish the corresponding 2,3-dialkyl-2,3-dichlorothiiranes (5) nearly quantitatively. The alkaline hydrolysis of 5 afforded 2,3-dialkylthiirene 1-oxides (10) in high yields. These two reactions could be successively carried out in one flask, and 2,3-di-tert-butyl-, 2,3-di-(1-adamantyl)-, and 2-(1-adamantyl)-3-tert-butylthiirene 1-oxides (10a–c) were obtained in 70, 80, and 90% yields, respectively, based on the starting acetylenes, thus providing the most convenient synthesis of thiirene 1-oxides. DiSulfur Dichloride also reacted with acetylenes to give 5 in good yields with the elimination of one Sulfur atom. Although the alkaline hydrolysis of 5 provided 10 exclusively, acid hydrolysis gave a mixture of α-oxothioketone 9 and thiirene 1-oxide 10 in modest yields. All thiirene 1-oxides 10a–c isomerized to produce α-oxothioketones 9 in high yields when heated in boiling toluene. Reactions of a bis-acetylene (18) with diSulfur Dichloride and with Sulfur Dichloride gave a dihydropentathiepin (19) in high yields. © 2002 Wiley Periodicals, Inc. Heteroatom Chem 13:424–430, 2002; Published online in Wiley Interscience (www.interscience.wiley.com). DOI 10.1002/hc.10070
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a convenient synthesis of thiirene 1 oxides
Tetrahedron Letters, 2001Co-Authors: Juzo Nakayama, Yoshiaki Sugihara, Kenta Takahashi, Akihiko IshiiAbstract:Abstract Acetylenes ( 1 ), carrying two bulky alkyl substituents, reacted with Sulfur Dichloride (ClSCl) to give 2,3-dialkyl-2,3-dichlorothiiranes ( 2 ) nearly quantitatively. The alkaline hydrolysis of crude 2 resulted in the formation of thiirene 1-oxides ( 3 ) in 68–90% yields based on 1 , thus providing a convenient synthesis of 3 .
Manfred Mühlstädt - One of the best experts on this subject based on the ideXlab platform.
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Darstellung und Reaktionen von β-Oxosulfenylchloriden. II. Direkte Chlorsulfanylierung von disubstituierten Acetaldehyden mit Schwefeldichlorid
Journal Fur Praktische Chemie-chemiker-zeitung, 2004Co-Authors: Manfred Mühlstädt, H. Meinhold, Dieter Martinetz, Eberhard NeumannAbstract:Preparation and Reactions of β-Oxosulfenyl Chlorides. II. Direct Chlorosulfenylation of Disubstituted Acetaldehydes by Sulfur Dichloride The reaction of dialkylacetaldehydes (1a, b) with Sulfur Dichloride yields the corresponding β-oxosulfenylchlorides (2a, b). Examples for addition- and substitution-reactions of 2a, b are described.
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Zur Molekülverknüpfung mit Schwefelchloriden. X. Bis(arylamino‐chloralkyl)‐sulfane aus N‐β‐Methallyl‐N‐tosyl‐anilinen und Schwefeldichlorid
Journal Fur Praktische Chemie-chemiker-zeitung, 2004Co-Authors: Kerstin Hollmann, M. Ecke, Manfred MühlstädtAbstract:Molecule Linkage by Sulfur Chlorides. X. Bis(arylamino-chloroalkyl)-sulfanes from N-β-Methallyl-N-tosyl-anilines and Sulfur Dichloride Reactions of differently substituted N-β-methallyl-N-tosyl-anilines 1 with Sulfur Dichloride yield bis(arylamino-chloroalkyl)-sulfanes 2 and 3 and dihydrobenzo-1,4-thiazines 4. The structural assignment of the products 2 and 3 was carried out by mass spectroscopy and 1H-n.m.r.-spectroscopy.
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Zur Molekülverknüpfung mit Schwefelchloriden. IV. Die Addition von Dichlorsulfan an Allyl-phenyl-äther. Anti-Markovnikov-Struktur der 1:2-Addukte†
Journal Fur Praktische Chemie-chemiker-zeitung, 2004Co-Authors: Manfred Mühlstädt, N. Stransky, E. Kleinpeter, H. MeinholdAbstract:Molecule Linkage by Sulfur Chlorides. IV. The Addition Reaction of Dichlorosulfane with Allyl-phenyl-ethers. Anti-Markovnikov-Structure of the 1:2 - Adducts Allyl-phenyl-ethers react with dichlorosulfane (Sulfur Dichloride) to anti-Markovnikov-adducts. This was demonstrated by the 1H-n.m.r. spectra and dehydrohalogenation of the isolated bis-(β-chloroalkyl)-thio ethers.
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Zur Molekülverknüpfung mit Schwefelchloriden. IX. Reaktion von Schwefeldichlorid mit N-Allyl-anilinen. Eine Synthese für 2-Chlormethyl-2,3-dihydro-1,4-benzothiazine†
Journal Fur Praktische Chemie-chemiker-zeitung, 2004Co-Authors: Manfred Mühlstädt, Kerstin Hollmann, M. MöderAbstract:Molecule Linkage by Sulfur Chlorides. IX. The Addition Reaction of Sulfur Dichlorides with N-Allyl-anilines. A Synthesis for 2-Chloromethyl-2,3-dihydrobenzo-1,4-thiazines Reactions of different substituted N-allyl-anilines 1 with Sulfur Dichloride yield 2-chloromethyl-2,3-dihydrobenzo-1,4-thiazines 3a–i. The identification of the products was carried out by mass spectroscopy and 1H-n.m.r.-spectroscopy. The seven-membered cyclic isomers of the S, N-heterocycles 3, dihydro-benzo-1,5-thiazepanes 5 were not obtained.
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Darstellung von Bis(1‐phenoxy‐propen‐2‐yl)‐sulfanen aus Bis(1‐chlor‐3‐phenoxy‐prop‐2‐yl)‐sulfanen mit Kalium‐tert.‐butylat – Zuordnung der E,E‐Konfiguration
Journal Fur Praktische Chemie-chemiker-zeitung, 2004Co-Authors: Kerstin Hollmann, M. Ecke, B. Habermann, Ina Schwope, Manfred MühlstädtAbstract:Synthesis of Bis(1-phenoxy-propen-2-yl)-sulfanes derived from Bis(1-chloro-3-phenoxy-prop-2-yl)-sulfanes with Potassium-tert.-butoxid – Determination of the E,E-Configuration Bis(1-chloro-3-phenoxy-prop-2-yl)-sulfanes (1), anti-MARKOVNIKOV 2:1-adducts of allylphenyl ethers with Sulfur Dichloride at low temperature are transformed in the presence of potassium-tert.-butoxid by dehydrohalogenation / prototropic rearrangement to phenoxyvinyl sulfanes, the E,E-bis(1-phenoxy-propen-2-yl)-sulfanes 3. Sulfanes 3 are of special interest as a model for unsaturated macrocycles B derivated from dithiacrown ethers A. The configuration was assigned using 1H-n.m.r.- and 13C-n.m.r.-spectroscopy. The molecular structure was determinded by X-ray diffraction techniques. Rearrangement of Sulfur-substituted allyl ethers 2 to the propenyl isomers 3a proceeds in a stereospecific manner as for common allyl ethers described in the literature.
K. A. Potekhin - One of the best experts on this subject based on the ideXlab platform.
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Reactions of Sulfur halides with unsaturated compounds. 26. Reactions of Sulfur Dichloride with tricyclo[4.2.2.0^2,5]deca-3,7-dienes and tricyclo[4.2.2.0^2,5]deca-3,7,9-trienes. Synthesis of compounds with a novel thiaskeletal structure
Bulletin of the Academy of Sciences of the USSR Division of chemical science, 1990Co-Authors: G A Tolstikov, B M Lerman, Yu T Struchkov, T. A. Belogaeva, D. S. Yufit, K. A. PotekhinAbstract:Addition of Sulfur Dichloride to tricyclo[4.2.2.0^2, 5]deca-3,7-dienes and tricyclo[4.2.2.0^2,5] deca-3,7,9-trienes is accompanied by intramolecular cyclization to give high yields of adducts with the novel thiaskeletal 7-thiatetracyclo[4.2.2.0^4,8.0^5,10]undecane structure. In the reaction of SCl_2 with the 2,3-endo, endo-diester (V), intramolecular cyclization is accompanied by lactonization, to give quantitative yields of the thiaskeletal chlorolactone (X). The structure of the latter compounds was established by x-ray diffraction examination.
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reactions of Sulfur halides with unsaturated compounds 26 reactions of Sulfur Dichloride with tricyclo 4 2 2 02 5 deca 3 7 dienes and tricyclo 4 2 2 02 5 deca 3 7 9 trienes synthesis of compounds with a novel thiaskeletal structure
Russian Chemical Bulletin, 1990Co-Authors: G A Tolstikov, B M Lerman, Yu T Struchkov, T. A. Belogaeva, D. S. Yufit, K. A. PotekhinAbstract:Addition of Sulfur Dichloride to tricyclo[4.2.2.02, 5]deca-3,7-dienes and tricyclo[4.2.2.02,5] deca-3,7,9-trienes is accompanied by intramolecular cyclization to give high yields of adducts with the novel thiaskeletal 7-thiatetracyclo[4.2.2.04,8.05,10]undecane structure. In the reaction of SCl2 with the 2,3-endo, endo-diester (V), intramolecular cyclization is accompanied by lactonization, to give quantitative yields of the thiaskeletal chlorolactone (X). The structure of the latter compounds was established by x-ray diffraction examination.
Kenta Takahashi - One of the best experts on this subject based on the ideXlab platform.
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practical synthesis of thiirene 1 oxides that possess two bulky alkyl substituents
Heteroatom Chemistry, 2002Co-Authors: Juzo Nakayama, Yoshiaki Sugihara, Kenta Takahashi, Michiyo Morita, Akihiko IshiiAbstract:Acetylenes that possess two bulky alkyl substituents reacted with Sulfur Dichloride to furnish the corresponding 2,3-dialkyl-2,3-dichlorothiiranes (5) nearly quantitatively. The alkaline hydrolysis of 5 afforded 2,3-dialkylthiirene 1-oxides (10) in high yields. These two reactions could be successively carried out in one flask, and 2,3-di-tert-butyl-, 2,3-di-(1-adamantyl)-, and 2-(1-adamantyl)-3-tert-butylthiirene 1-oxides (10a–c) were obtained in 70, 80, and 90% yields, respectively, based on the starting acetylenes, thus providing the most convenient synthesis of thiirene 1-oxides. DiSulfur Dichloride also reacted with acetylenes to give 5 in good yields with the elimination of one Sulfur atom. Although the alkaline hydrolysis of 5 provided 10 exclusively, acid hydrolysis gave a mixture of α-oxothioketone 9 and thiirene 1-oxide 10 in modest yields. All thiirene 1-oxides 10a–c isomerized to produce α-oxothioketones 9 in high yields when heated in boiling toluene. Reactions of a bis-acetylene (18) with diSulfur Dichloride and with Sulfur Dichloride gave a dihydropentathiepin (19) in high yields. © 2002 Wiley Periodicals, Inc. Heteroatom Chem 13:424–430, 2002; Published online in Wiley Interscience (www.interscience.wiley.com). DOI 10.1002/hc.10070
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a convenient synthesis of thiirene 1 oxides
Tetrahedron Letters, 2001Co-Authors: Juzo Nakayama, Yoshiaki Sugihara, Kenta Takahashi, Akihiko IshiiAbstract:Abstract Acetylenes ( 1 ), carrying two bulky alkyl substituents, reacted with Sulfur Dichloride (ClSCl) to give 2,3-dialkyl-2,3-dichlorothiiranes ( 2 ) nearly quantitatively. The alkaline hydrolysis of crude 2 resulted in the formation of thiirene 1-oxides ( 3 ) in 68–90% yields based on 1 , thus providing a convenient synthesis of 3 .
