Carbon-carbon bond cleavage and iminocarbene formation in the thermal decomposition of 2H-azirines

1974 ◽  
Vol 96 (1) ◽  
pp. 308-309 ◽  
Author(s):  
Larry A. Wendling ◽  
Robert G. Bergman
Keyword(s):  
Thermal Decomposition ◽  
Bond Cleavage ◽  
Carbon Bond ◽  
Carbon Carbon Bond

Reaction of methyl azidoformate with norbornene

1969 ◽  
Vol 47 (23) ◽  
pp. 4367-4374 ◽  
Author(s):  
A. C. Oehlschlager ◽  
R. S. McDaniel ◽  
A. Thakore ◽  
P. Tillman ◽  
L. H. Zalkow
Keyword(s):  
Thermal Decomposition ◽  
Bond Cleavage ◽  
Thermal Reaction ◽  
Dipolar Cycloaddition ◽  
Carbon Bond ◽  
Heterolytic Cleavage ◽  
Carbon Carbon Bond ◽  
Step Mechanism

The thermal reaction of methyl azidoformate and norbornene has been found to proceed via 1,3-dipolar-cycloaddition yielding exo triazoline adduct, 15a. Thermal decomposition of the triazoline results in the loss of nitrogen and the formation of at least 5 products. The major products of the thermal decomposition in decalin were 3-carbomethoxy-3-azatricyclo(3.2.1.02,4 exo)octane, 18a, and N-carbomethoxy-2-norbornimine, 20. In addition, syn-2-norbornene-7-methyl carbamate, 21, and 3-carbomethoxy-3-azatricyclo(3.2.1.02,3 endo)octane, 19a, were isolated. The thermal decomposition of the triazoline adduct is considered to proceed by a multi-step mechanism. The first step is considered to involve heterolytic cleavage of the N3—N4 bond togive a zwitterion which may lead to products or rearrange via carbon–carbon bond cleavage to give a diazoalkyl imine.

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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