ChemInform Abstract: ANODIC RING OPENING REACTION OF 2-METHOXY-1-CYCLOPENTENE-1-CARBOXYLIC ACIDS

1973 ◽  
Vol 4 (44) ◽  
pp. no-no
Author(s):  
SIGERU TORII ◽  
HIDEO TANAKA ◽  
TOKIO FUKUOKA ◽  
SHUKUO HIRAI
Keyword(s):  
Carboxylic Acids ◽  
Ring Opening ◽  
Ring Opening Reaction

scholarly journals Anodic Ring Opening Reaction of 2-Methoxy-1-cyclopentene-1-carboxylic Acids

1973 ◽  
Vol 46 (8) ◽  
pp. 2534-2537 ◽  
Author(s):  
Sigeru Torii ◽  
Hideo Tanaka ◽  
Tokio Fukuoka ◽  
Shukuo Hirai
Keyword(s):  
Carboxylic Acids ◽  
Ring Opening ◽  
Ring Opening Reaction

Efficient and Regioselective Ring-opening of Epoxides with Carboxylic Acid Catalyzed by Graphite Oxide

2020 ◽  
Vol 17 (7) ◽  
pp. 532-538
Author(s):  
Maryam Mirza-Aghayan ◽  
Mahdieh Molaee Tavana ◽  
Elaheh Golam Alipour Niazi ◽  
Rabah Boukherroub
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Graphite Oxide ◽  
Ring Opening ◽  
Reaction Times ◽  
Metal Free ◽  
Ring Opening Reaction ◽  
Ring Opening Of Epoxides ◽  
Acid Catalyzed

An efficient, simple and regioselective ring-opening reaction of epoxides with various carboxylic acids under metal-free conditions is reported. The ring-opening of epoxides takes place in the presence of graphite oxide as an efficient and available catalyst to produce the corresponding 2-hydroxy monoester and 1,2-diester derivatives in good yields. Regioselective attack of the nucleophile, short reaction times, metal-free conditions and reusability of catalyst are among the advantages of the present protocol.

On the Conrotatory Ring Opening of 3-Carbomethoxycyclobutene Vis-À-Vis 3-Carbomethoxy-1,2-Benzocyclobutene and the Predominant Inward Opening of 3-Dimethylaminocarbonyl-1,2-Benzocyclobutene

2018 ◽  
Author(s):  
Veejendra Yadav ◽  
Dasari L V K Prasad ◽  
Arpita Yadav ◽  
Maddali L N Rao
Keyword(s):  
Transition State ◽  
Ring Opening ◽  
Electron Process ◽  
Ring Opening Reaction ◽  
Stable Species ◽  
Electron Event

<p>The torquoselectivity of conrotatory ring opening of 3-carbomethoxycyclobutene is controlled by p<sub>C1C2</sub>→s*<sub>C3C4</sub> and s<sub>C3C4</sub>→p*<sub>CO</sub> interactions in the transition state in a 4-electron process as opposed to only s<sub>C3C4</sub>→p*<sub>CO</sub> interaction in an apparently 8-electron event in 3-carbomethoxy-1,2-benzocyclobutene. The ring opening of 3-carbomethoxy-1,2-benzocyclobutene is sufficiently endothermic. We therefore argue that the reverse ring closing reaction is faster than the forward ring opening reaction and, thus, it establishes an equilibrium between the two and subsequently allows formation of the more stable species <i>via</i> outward ring opening reaction. Application of this argument to 3-dimethylaminocarbonyl-1,2-benzocyclobutene explains the predominantly observed inward opening.</p>

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