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Blagoev, Milen; Linden, Anthony; Heimgartner, Heinz

doi:10.1002/1522-2675(20001220)83:12<3163::aid-hlca3163>3.3.co;2-g

“…In some cases, 1,3-dithiolanes and 1,3-dioxolanes are formed in addition to 1,3-oxathiolanes [4,6,7]. For example, the BF 3 -catalyzed reaction of thiobenzophenone (13a) and 1,2-epoxycyclohexane (15) in dichloromethane at -50°C yields 16, 17a, and 17b [6].…”

Section: Methodsmentioning

confidence: 99%

Regio- and Stereoselective Formation of 1,3-Oxathiolanes by Reactions of Thiocarbonyl Compounds with Oxiranes

Heimgartner

¹

,

Fu

²

,

Blagoev

³

et al. 2005

Phosphorus, Sulfur, and Silicon and the Related Elements

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Lewis acid-catalyzed reactions of oxiranes with a variety of C=S compounds yield 1,3-oxathiolanes. The ring enlargement of monosubstituted oxiranes occurs regioselectively via cleavage of the O,C(3) bond of alkyl substituted oxiranes and the O,C(2) bond of phenyl oxirane. Furthermore, the reaction proceeds with inversion of the configuration at the center of the nucleophilic attack by the S-atom. The formation of thiocarbonylium ions as intermediates is supported by Wagner-Meerwein-type rearrangements. Enolized thioketones react with oxiranes to give enesulfanyl alcohols, which undergo an acid-catalyzed cyclization to yield 1,3-oxathiolanes. Lewis acid-catalyzed reactions of oxiranes with a variety of C=S compounds yield 1,3-oxathiolanes. The ring enlargement of monosubstituted oxiranes occurs regioselectively via cleavage of the O,C(3) bond of alkyl substituted oxiranes and the O,C(2) bond of phenyl oxirane. Furthermore, the reaction proceeds with inversion of the configuration at the center of the nucleophilic attack by the S-atom. The formation of thiocarbonylium ions as intermediates is supported by Wagner-Meerwein type rearrangements. Enolized thioketones react with oxiranes to give enesulfanyl alcohols, which undergo an acid-catalyzed cyclization to yield 1,3-oxathiolanes. REGIO-AND STEREOSELECTIVE FORMATION OF 1,3-OXATHIOLANES BY REACTIONS OF THIOCARBONYL COMPOUNDS WITH OXIRANES

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“…In some cases, 1,3-dithiolanes and 1,3-dioxolanes are formed in addition to 1,3-oxathiolanes [4,6,7]. For example, the BF 3 -catalyzed reaction of thiobenzophenone (13a) and 1,2-epoxycyclohexane (15) in dichloromethane at -50°C yields 16, 17a, and 17b [6].…”

Section: Methodsmentioning

confidence: 99%

Regio‐ and Stereoselective Formation of 1,3‐Oxathiolanes by Reactions of Thiocarbonyl Compounds with Oxiranes

Fu¹,

Blagoev²,

Linden³

et al. 2005

ChemInform

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0

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Lewis acid-catalyzed reactions of oxiranes with a variety of C=S compounds yield 1,3-oxathiolanes. The ring enlargement of monosubstituted oxiranes occurs regioselectively via cleavage of the O,C(3) bond of alkyl substituted oxiranes and the O,C(2) bond of phenyl oxirane. Furthermore, the reaction proceeds with inversion of the configuration at the center of the nucleophilic attack by the S-atom. The formation of thiocarbonylium ions as intermediates is supported by Wagner-Meerwein-type rearrangements. Enolized thioketones react with oxiranes to give enesulfanyl alcohols, which undergo an acid-catalyzed cyclization to yield 1,3-oxathiolanes. Lewis acid-catalyzed reactions of oxiranes with a variety of C=S compounds yield 1,3-oxathiolanes. The ring enlargement of monosubstituted oxiranes occurs regioselectively via cleavage of the O,C(3) bond of alkyl substituted oxiranes and the O,C(2) bond of phenyl oxirane. Furthermore, the reaction proceeds with inversion of the configuration at the center of the nucleophilic attack by the S-atom. The formation of thiocarbonylium ions as intermediates is supported by Wagner-Meerwein type rearrangements. Enolized thioketones react with oxiranes to give enesulfanyl alcohols, which undergo an acid-catalyzed cyclization to yield 1,3-oxathiolanes. REGIO-AND STEREOSELECTIVE FORMATION OF 1,3-OXATHIOLANES BY REACTIONS OF THIOCARBONYL COMPOUNDS WITH OXIRANES

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“…This explanation is supported by the results obtained with 1 and cis-and trans-2,3-dimethyloxirane, respectively. 59 In this case, dispirocyclic 1:2 adducts are also formed by involvement of the carbonyl group of 1. The reaction of amino-9-fluorenylideneborane (68) with 1 occurs chemo-and regioselectively at the carbonyl group to give the 1,2-oxaboretane (69) (eq 29).…”

Section: %mentioning

confidence: 99%