Notizen: Umsetzung von Keten-N,N-acetalen mit aliphatischen Sulfochloriden

Opitz, G.; Schempp, Heinrich

doi:10.1515/znb-1964-0123

Cited by 8 publications

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“…Reaction of phenylmethanesulfonyl chloride with [(1-ethoxy-2-methyl-1-propenyl)oxy]trimethylsilane and subsequent hydrolysis gave the thietan-3-one-1,1-dioxide 301 (R 1 , R 2 = CH 3 ; R 3 = H, R 4 = C 6 H 5 ) . The hydrolysis of 3-(dialkylamino)thiete-1,1-dioxides 302 also resulted in the formation of the corresponding thietan-3-one-1,1-dioxides 303 . − ,− The 3-dialkylaminothiete-1,1-dioxides 302 were obtained from the cycloaddition of alkylsulfonyl chlorides and ketene O,N-acetals or aminals 180-183,209 or from the cycloaddition of alkylsulfonyl chlorides and alkynylamines . Many different compounds 302 have been synthesized in this way.…”

Section: A Synthetic Methods For Thietan-3-onesa1 Synthesis From Acyc...mentioning

confidence: 99%

“…Many different compounds 302 have been synthesized in this way. The hydrolysis was performed with an acidic exchange resin (Amberlite IR-120) 180,181,206 or concentrated hydrochloric acid in water. , …”

Section: A Synthetic Methods For Thietan-3-onesa1 Synthesis From Acyc...mentioning

confidence: 99%

“…204 The hydrolysis of 3-(dialkylamino)thiete-1,1-dioxides 302 also resulted in the formation of the corresponding thietan-3-one-1,1-dioxides 303. [180][181][182][205][206][207][208][209] The 3-dialkylaminothiete-1,1-dioxides 302 were obtained from the cycloaddition of alkylsulfonyl chlorides and ketene O,N-acetals or aminals [180][181][182][183]209 or from the cycloaddition of alkylsulfonyl chlorides and alkynylamines. 206 Many different compounds 302 have been synthesized in this way.…”

Section: A1 Synthesis From Acyclic Precursorsmentioning

confidence: 99%

“…The hydrolysis was performed with an acidic exchange resin (Amberlite IR-120) 180,181,206 or concentrated hydrochloric acid in water. 207,209 Thietan-3-ones were also obtained by the cycloaddition reaction between 1,1,1,3,3,3-hexafluoro-2-propanethione 305 and diphenylketene, which gave compound 306 via a [2+2] cycloaddition reaction (Scheme 82). 210 The cycloaddition of thiobenzophenone and diphenylketene has been reported to give 2,2,4,4-tetraphenylthietan-3-one in 85% yield.…”

Section: A1 Synthesis From Acyclic Precursorsmentioning

confidence: 99%

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The Chemistry of Azetidin-3-ones, Oxetan-3-ones, and Thietan-3-ones

et al. 2001

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I. Introduction 29 II. The Chemistry of Azetidin-3-ones 29 A. Structural Data 29 B. Synthetic Methods for Azetidin-3-ones 31 B.1. Carbonyl Group Generation in the Azetidine Ring 31 B.2. Intramolecular Cyclization Reactions 34 B.3. 1,3-Dipolar Cycloaddition Reactions 36 C. Chemical Properties of Azetidin-3-ones 37 C.1. Transformations of the Carbonyl Group 37 C.2. Condensation Reactions − Synthesis of 2-Benzylideneazetidin-3-ones 40 C.3. Ring Transformations of Azetidin-3-ones 40 C.4. Miscellaneous 41 III. The Chemistry of Oxetan-3-ones 42 A. Structural Data 42 B. Synthetic Methods for Oxetan-3-ones 43 B.1. Decomposition of Diazoketones 43 B.2. Oxidation Reactions 44 B.3. Intramolecular Displacement Reactions 46 B.4. Miscellaneous 47 C. Chemical Properties of Oxetan-3-ones 48 C.1. Ring Opening and Ring Expansion of Oxetan-3-ones 48 C.2. Transformations of the Carbonyl Group 49 IV. The Chemistry of Thietan-3-ones 50 A. Synthetic Methods for Thietan-3-ones 51 A.1. Synthesis from Acyclic Precursors 51 A.2. Synthesis by Ring Transformations 53 B. Chemical Properties of Thietan-3-ones 54 B.1. Transformations of the Carbonyl Group 55 B.2. Aldol Reactions 56 B.3. Ring Transformations 56 V. Acknowledgments 58 VI. References 58

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