Vinyl sulfide hydrolysis

The hydrolysis of vinyl sulfides in acid solutions is shown to proceed via a mechanism analogous to that of vinyl ethers, with slow proton transfer to the carbon–carbon double bond to produce a sulfur stabilized carbonium ion. Relative rates of hydrolysis of compounds RXCH=CH2 are CH3S—, 41; CH3O—, 1500; C6H5S—, 1; and C6H5O—, 10.5. This order is compared with that of other systems which produce similar stabilized carbonium ions.

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Acid-catalyzed hydrolysis of a phenylketene dithioacetal. Reversible protonation of the carbon-carbon double bond

Journal of the American Chemical Society ◽

10.1021/ja00351a044 ◽

1983 ◽

Vol 105 (13) ◽

pp. 4390-4395 ◽

Cited By ~ 9

Author(s):

Tadashi Okuyama ◽

Takayuki Fueno

Keyword(s):

Double Bond ◽

Carbon Double Bond ◽

Acid Catalyzed ◽

Hydrolysis Of

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ChemInform Abstract: ACID-CATALYZED HYDROLYSIS OF A PHENYLKETENE DITHIOACETAL. REVERSIBLE PROTONATION OF THE CARBON-CARBON DOUBLE BOND

Chemischer Informationsdienst ◽

10.1002/chin.198341081 ◽

1983 ◽

Vol 14 (41) ◽

Author(s):

T. OKUYAMA ◽

T. FUENO

Keyword(s):

Double Bond ◽

Carbon Double Bond ◽

Acid Catalyzed ◽

Hydrolysis Of

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RNA-Seq used to identify ipsdienone reductase (IDONER): A novel monoterpene carbon-carbon double bond reductase central to Ips confusus pheromone production

Insect Biochemistry and Molecular Biology ◽

10.1016/j.ibmb.2020.103513 ◽

2021 ◽

pp. 103513

Author(s):

Katherine E. Fisher ◽

Richard L. Tillett ◽

Misha Footohi ◽

Cody Caldwell ◽

Juli Petereit ◽

...

Keyword(s):

Double Bond ◽

Pheromone Production ◽

Rna Seq ◽

Ips Confusus ◽

Carbon Double Bond ◽

Double Bond Reductase

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Reactions of 4-Pyrones with Azomethine Ylides as a Chemoselective Method for the Construction of Multisubstituted Pyrano[2,3-c]pyrrolidines

Synthesis ◽

10.1055/s-0040-1706032 ◽

2021 ◽

Author(s):

Dmitrii L. Obydennov ◽

Vyacheslav D. Steben’kov ◽

Konstantin L. Obydennov ◽

Sergey A. Usachev ◽

Vladimir S. Moshkin ◽

...

Keyword(s):

Double Bond ◽

Ring Opening ◽

Azomethine Ylides ◽

Azomethine Ylide ◽

Dipolar Cycloaddition ◽

Computational Studies ◽

Carbon Double Bond ◽

Reactivity Indexes ◽

Reaction Proceeds

Abstract4-Pyrones bearing electron-donating and electron-withdrawing groups react with nonstabilized azomethine ylides to form pyrano[2,3-c]pyrrolidines in moderate to good yields. The reaction proceeds chemoselectively as a 1,3-dipolar cycloaddition of the azomethine ylide at the carbon–carbon double bond of the pyrone activated by the electron-withdrawing substituent. The reactivity of 4-pyrones toward azomethine ylides was rationalized by computational studies with the use of reactivity indexes. The pyrano[2,3-c]pyrrolidine moiety could be modified, for example by a ring-opening transformation under the action of hydrazine to provide pyrazolyl-substituted pyrrolidines.

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