Ring Opening of Cyclic Vinylogous Acyl Triflates Using Stabilized Carbanion Nucleophiles: Claisen Condensation Linked to Carbon−Carbon Bond Cleavage

2010 ◽  
Vol 75 (10) ◽  
pp. 3260-3267 ◽  
Author(s):  
David M. Jones ◽  
Marilda P. Lisboa ◽  
Shin Kamijo ◽  
Gregory B. Dudley
Keyword(s):  
Ring Opening ◽  
Bond Cleavage ◽  
Carbon Bond ◽  
Claisen Condensation ◽  
Carbon Carbon Bond

Base-catalyzed ring openings of benzocyclobutenones and -ols

1995 ◽  
Vol 73 (10) ◽  
pp. 1660-1665 ◽  
Author(s):  
J.C. Bradley ◽  
T. Durst
Keyword(s):  
Ring Opening ◽  
Bond Cleavage ◽  
Aprotic Solvents ◽  
Carbon Bond ◽  
Protic Solvents ◽  
Carbon Carbon Bond

The base-catalyzed ring opening of a number of isomeric E-and Z-benzylidenebenzocyclobutenones and -ols has been studied in both protic and aprotic solvents. Cleavage of the C1—C2 bond results in the formation of stilbenes with mainly, and at times exclusively, retained stereochemistry. For the alcohols, these results point to an oxyanion-induced carbon–carbon bond cleavage leading to a vinyl anion that is protonated with retention of configuration in the protic solvents rather than to an electrocyclic ring opening to an alkoxy o-quinodimethane. Reaction of the Z isomer of benzylidenebenzocyclobutenol with methyllithium in THF at 20 °C causes isomerization to the E isomer, cleavage of the C1—C2 bond, and recyclization of the resultant isomerized vinyl anion. Keywords: benzylidenebenzocyclobutenones, base-catalyzed ring opening; benzylidenebenzocyclobutenols, base-catalyzed ring opening.

Synthesis of 2-(Cyanomethyl)benzoic Esters via Carbon–Carbon Bond Cleavage of Indanones

2021 ◽  
Author(s):  
Xiangtai Meng ◽  
Dengfeng Chen ◽  
Rui Liu ◽  
Ping Jiang ◽  
Shenlin Huang
Keyword(s):  
Bond Cleavage ◽  
Carbon Bond ◽  
Carbon Carbon Bond

Aerobic Dehydrogenative α-Diarylation of Benzyl Ketones with Aromatics through Carbon–Carbon Bond Cleavage

2014 ◽  
Vol 16 (3) ◽  
pp. 804-807 ◽  
Author(s):  
Nagnath Yadav More ◽  
Masilamani Jeganmohan
Keyword(s):  
Bond Cleavage ◽  
Carbon Bond ◽  
Carbon Carbon Bond
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