Anti-Markovnikov addition to alkenes with a neighbouring thioacetal function
The acid-induced cyclisation of unsaturated thioacetals gives pyrans as anti-Markovnikov products, apparently involving sulfur elimination and readdition. The acid-induced cyclisation of unsaturated thioacetals 6 gives anti-Markovnikov products 9, apparently involving sulfur elimination and readditi...
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Published in | Tetrahedron letters Vol. 47; no. 27; pp. 4549 - 4551 |
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Main Authors | , , , |
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Language | English |
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Abstract | The acid-induced cyclisation of unsaturated thioacetals gives pyrans as anti-Markovnikov products, apparently involving sulfur elimination and readdition.
The acid-induced cyclisation of unsaturated thioacetals
6 gives anti-Markovnikov products
9, apparently involving sulfur elimination and readdition. |
---|---|
AbstractList | The acid-induced cyclisation of unsaturated thioacetals gives pyrans as anti-Markovnikov products, apparently involving sulfur elimination and readdition.
The acid-induced cyclisation of unsaturated thioacetals
6 gives anti-Markovnikov products
9, apparently involving sulfur elimination and readdition. The acid-induced cyclisation of unsaturated thioacetals 6 gives anti-Markovnikov products 9, apparently involving sulfur elimination and readdition. (c) 2006 Elsevier Ltd. All rights reserved. |
Author | Dreeßen, Sylvia Tiedemann, Ralf Bongardt, Tim Schaumann, Ernst |
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Keywords | Markovnikov rule Cyclisation Regioselectivity Tetrahydrofurans Pyrans regioselectivity pyrans SYNTHETIC ROUTES tetrahydrofurans cyclisation RULES INDUCED CYCLIZATIONS |
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References | Baldwin, Thomas, Kruse, Silberman (bib5) 1977; 42 Boivin (bib1) 1987; 43 Adiwidjaja, Flörke, Kirschning, Schaumann (bib4) 1995 Schaumann, Kirschning, Narjes (bib6) 1991; 56 Aprile, Gruttadauria, Amato, D’Anna, Meo, Riela, Noto (bib9) 2003; 59 Harmange, Figadère (bib3) 1993; 4 Johnson (bib7) 1993; 26 Schaumann, Narjes, Tiedemann (bib8) 1994; 95/96 Trost, Murayama, Trost, Sato (bib10) 1981; 103 Elliott, Willams (bib2) 2001 ADIWIDJAJA, G (WOS:A1995QN72800009) 1995 Aprile, C (WOS:000181731500006) 2003; 59 SCHAUMANN, E (WOS:A1994QX42600036) 1994; 95-6 Elliott, MC (WOS:000171794000001) 2001 BOIVIN, TLB (WOS:A1987J990600001) 1987; 43 BALDWIN, JE (WOS:A1977EC23200011) 1977; 42 HARMANGE, JC (WOS:A1993LT06300002) 1993; 4 TROST, BM (WOS:A1985ABE0400043) 1985; 107 SCHAUMANN, E (WOS:A1991EU10800043) 1991; 56 TROST, BM (WOS:A1981ML44100058) 1981; 103 JOHNSON, CD (WOS:A1993LX34100004) 1993; 26 Adiwidjaja (10.1016/j.tetlet.2006.05.009_bib4) 1995 Trost (10.1016/j.tetlet.2006.05.009_bib10_1) 1981; 103 Elliott (10.1016/j.tetlet.2006.05.009_bib2) 2001 Schaumann (10.1016/j.tetlet.2006.05.009_bib8) 1994; 95/96 Boivin (10.1016/j.tetlet.2006.05.009_bib1) 1987; 43 Baldwin (10.1016/j.tetlet.2006.05.009_bib5) 1977; 42 Aprile (10.1016/j.tetlet.2006.05.009_bib9) 2003; 59 Johnson (10.1016/j.tetlet.2006.05.009_bib7) 1993; 26 Harmange (10.1016/j.tetlet.2006.05.009_bib3) 1993; 4 Schaumann (10.1016/j.tetlet.2006.05.009_bib6) 1991; 56 Trost (10.1016/j.tetlet.2006.05.009_bib10_2) 1985; 107 |
References_xml | – volume: 95/96 start-page: 347 year: 1994 ident: bib8 publication-title: Phosphorus, Sulfur, and Silicon contributor: fullname: Tiedemann – start-page: 2303 year: 2001 end-page: 2340 ident: bib2 publication-title: J. Chem. Soc., Perkin. Trans. 1 contributor: fullname: Willams – volume: 56 start-page: 717 year: 1991 end-page: 723 ident: bib6 publication-title: J. Org. Chem. contributor: fullname: Narjes – volume: 59 start-page: 2241 year: 2003 end-page: 2251 ident: bib9 publication-title: Tetrahedron contributor: fullname: Noto – start-page: 501 year: 1995 end-page: 507 ident: bib4 publication-title: Liebigs. Ann. contributor: fullname: Schaumann – volume: 26 start-page: 476 year: 1993 end-page: 482 ident: bib7 publication-title: Acc. Chem. Res. contributor: fullname: Johnson – volume: 43 start-page: 3309 year: 1987 end-page: 3362 ident: bib1 publication-title: Tetrahedron contributor: fullname: Boivin – volume: 42 start-page: 3846 year: 1977 end-page: 3852 ident: bib5 publication-title: J. Org. Chem. contributor: fullname: Silberman – volume: 103 start-page: 6529 year: 1981 end-page: 6530 ident: bib10 publication-title: J. Am. Chem. 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Soc. doi: 10.1021/ja00411a058 contributor: fullname: Trost – volume: 43 start-page: 3309 year: 1987 ident: 10.1016/j.tetlet.2006.05.009_bib1 publication-title: Tetrahedron doi: 10.1016/S0040-4020(01)81626-4 contributor: fullname: Boivin – volume: 4 start-page: 1711 year: 1993 ident: 10.1016/j.tetlet.2006.05.009_bib3 publication-title: Tetrahedron: Asymmetry doi: 10.1016/S0957-4166(00)80408-5 contributor: fullname: Harmange – volume: 95/96 start-page: 347 year: 1994 ident: 10.1016/j.tetlet.2006.05.009_bib8 publication-title: Phosphorus, Sulfur, and Silicon doi: 10.1080/10426509408034232 contributor: fullname: Schaumann – start-page: 501 year: 1995 ident: 10.1016/j.tetlet.2006.05.009_bib4 publication-title: Liebigs. Ann. doi: 10.1002/jlac.199519950369 contributor: fullname: Adiwidjaja |
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Snippet | The acid-induced cyclisation of unsaturated thioacetals gives pyrans as anti-Markovnikov products, apparently involving sulfur elimination and readdition.
The... The acid-induced cyclisation of unsaturated thioacetals 6 gives anti-Markovnikov products 9, apparently involving sulfur elimination and readdition. (c) 2006... |
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SubjectTerms | Chemistry Chemistry, Organic Cyclisation Markovnikov rule Physical Sciences Pyrans Regioselectivity Science & Technology Tetrahydrofurans |
Title | Anti-Markovnikov addition to alkenes with a neighbouring thioacetal function |
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