Alkynylamines with sulfenes

Rosen, Melvin

doi:10.1016/s0040-4039(01)87772-8

Cited by 8 publications

(7 citation statements)

References 11 publications

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“…Reaction of thietan-3-one with secondary amines such as morpholine did not give enamines but the ring opened 2-oxopropionthioamides . The same reaction performed on 2-methylthietan-3-one-1,1-dioxides gave ring opening to the N , N -dialkyl-2-(methylsulfonyl)acetamides . The reaction of thietan-3-one-1,1-dioxide 360 with primary amines afforded the products 362 or 363 via the intermediate 361 .…”

Section: B3 Ring Transformationsmentioning

confidence: 93%

“…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%

“…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%

“…[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. The hydrolysis was performed with an acidic exchange resin (Amberlite IR-120) 180,181,206 or concentrated hydrochloric acid in water.…”

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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Section: B3 Ring Transformationsmentioning

confidence: 93%

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

confidence: 99%

Section: A1 Synthesis From Acyclic Precursorsmentioning

confidence: 99%

Section: A1 Synthesis From Acyclic Precursorsmentioning

confidence: 99%

See 2 more Smart Citations

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

et al. 2001

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“…9 unit. Upon hydrolysis in 10% aqueous NaOH compounds (7) give 3-substituted N-methyl-4-quinolones (8).…”

Section: Reactions Of Ynamines With Iminium Salts[llmentioning

confidence: 99%

Reactions of Ynamines with Iminium Salts

Fuks

King

Viehe

1969

Angew. Chem. Int. Ed. Engl.

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Bis(N4luorosulfonylimido)sulfur difluoride [21 ( I ) reacts with dimethylamine in diethyl ether to give dimethylamidobis-(N-fluorosulfony1imido)sulfur fluoride (2). Dimethylamine (6.8 g, 0.15 mole) is passed into a stirred solution of ( I ) (18.5 g, 0.07 mole) in diethyl ether (300 ml) at -78 "C during 1 h. The reaction mixture is then warmed to room temperature and the ethereal phase separated off. Removal of the ether under reduced pressure and subsequent distillation of the residue at oil-pump vacuum affords 6 g Compound ( 2 ) is a colorless liquid (b.p. 115"C/0.01 torr) which was identified by elemental analysis and NMR spectroscopy. The 19F-NMR spectrum recorded at room temperature shows a doublet due to the fluorine atoms of the FSO2 groups, 8~~0~ = -60.3 pprn (CFC13 as external standard): JFF = 7.4Hz. The fluorine atom of the FSN3 group gives rise to a multiplet of intensity ratio 1:6:17:32:46: 52:46:32:17:6:1 by superposition of a triplet (FF coupling), which is split into three septets as a result of FH coupling. The intensity ratio FSO~:FSN, is 2 3 ; ~F S N , = -58.4 ppm.

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Methanesulfonyl Chloride

Vaillancourt

Cudahy

2001

Encyclopedia of Reagents for Organic Synthesis

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Alkynylamines with sulfenes

Cited by 8 publications

References 11 publications

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

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

Reactions of Ynamines with Iminium Salts

Methanesulfonyl Chloride

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