Formal Transfers of Hydride from Carbon−Hydrogen Bonds. Generation of H2from Orthoformamides Designed To Undergo Intramolecular Protonolyses of Activated Carbon−Hydrogen Bonds

1996 ◽  
Vol 61 (6) ◽  
pp. 2020-2026 ◽  
Author(s):  
Philippe Brunet ◽  
James D. Wuest
Keyword(s):  
Activated Carbon ◽  
Hydrogen Bonds ◽  
Carbon Hydrogen Bonds

Formal transfers of hydride from carbon–hydrogen bonds. Attempted generation of H2 by intramolecular protonolyses of the activated carbon–hydrogen bonds of dihydrobenzimidazoles

1996 ◽  
Vol 74 (5) ◽  
pp. 689-696 ◽  
Author(s):  
Philippe Brunet ◽  
James D. Wuest
Keyword(s):  
Activated Carbon ◽  
Carboxylic Acid ◽  
Hydrogen Bonds ◽  
Key Words ◽  
Hydride Generation ◽  
Carboxylic Acid Groups ◽  
Lone Pairs ◽  
Close Proximity ◽  
Acidic Sites ◽  
Carbon Hydrogen Bonds

Protonolyses of carbon–hydrogen bonds can occur under suitable conditions to produce carbocations and H2. In an effort to accelerate these fundamental reactions, we have attempted to make them intramolecular by devising compounds in which carbon–hydrogen bonds designed to be particularly good formal donors of hydride are held in close proximity to acidic sites. Dihydrobenzimidazoles 4 and 11 are compounds of this type, since the carbon–hydrogen bonds at C2 are activated as formal donors of hydride by adjacent lone pairs in a dihydroaromatic ring, and acidic anilinium and carboxylic acid groups are held nearby. Unfortunately, this proximity does not lead to the formation of H2 by protonolysis; instead, other reactions intervene when compounds 4 and 11 are subjected to pyrolysis. Key words: intramolecular protonolysis of carbon–hydrogen bonds, formal donors of hydride, generation of H2, dihydrobenzimidazoles.

ChemInform Abstract: REACTION OF CHLORAL WITH COMPOUNDS CONTAINING ACTIVATED CARBON-HYDROGEN BONDS

1979 ◽  
Vol 10 (26) ◽  
Author(s):  
K. A. PETROV ◽  
N. A. TIKHONOVA ◽  
Z. YA. LAPSHINA ◽  
N. A. TIL'KUNOVA ◽  
N. N. BARANOV
Keyword(s):  
Activated Carbon ◽  
Hydrogen Bonds ◽  
Carbon Hydrogen Bonds
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