Mechanism of the Electrochemical Reduction of 3,5-Di-tert-butyl-1,2-benzoquinone. Evidence for a Concerted Electron and Proton Transfer Reaction Involving a Hydrogen-Bonded Complex as Reactant†

2001 ◽  
Vol 105 (37) ◽  
pp. 8877-8884 ◽  
Author(s):  
Mark W. Lehmann ◽  
Dennis H. Evans
Keyword(s):  
Proton Transfer ◽  
Electrochemical Reduction ◽  
Transfer Reaction ◽  
Proton Transfer Reaction ◽  
Tert Butyl ◽  
Hydrogen Bonded

A TDDFT study on the excited-state double proton transfer reaction of 8-hydroxyquinoline along a hydrogen-bonded bridge

2017 ◽  
Vol 41 (16) ◽  
pp. 8437-8442 ◽  
Author(s):  
Yu-Hui Liu ◽  
Shi-Ming Wang ◽  
Chaoyuan Zhu ◽  
Sheng Hsien Lin
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Transfer Reaction ◽  
Proton Transfer Reaction ◽  
Double Proton Transfer ◽  
Hydrogen Bonded

The mechanism of excited-state multiple proton transfer reaction is demonstrated to be controlled by a hydrogen-bonded bridge.

A 2-Azapentadienyl Carbanion: a Nonstereospecific Electrocyclization

1975 ◽  
Vol 53 (3) ◽  
pp. 355-365 ◽  
Author(s):  
D. H. Hunter ◽  
R. P. Steiner
Keyword(s):  
Proton Transfer ◽  
Transfer Reaction ◽  
Proton Transfer Reaction ◽  
Butyl Alcohol ◽  
Open Chain ◽  
Tert Butyl ◽  
Tert Butyl Alcohol ◽  
Cis And Trans ◽  
Protic Media

Treatment of 1,3,5-triphenyl-4-aza-1,3-pentadiene under selected basic conditions leads to either isomerization among the azapentadienes or to cyclization. Analysis of the products from reaction under aprotic conditions (LiTMP in THF) suggested that the open-chain delocalized carbanion exists in both the W and sickle forms. The open-chain anions were observed to electrocyclize in a nonstereospecific manner to produce a 1:1 mixture of cis- and trans-2,4,5-triphenyl-1-pyrrolines. Reaction in protic media (methanol and tert-butyl alcohol) produced a 1,5-proton transfer as well as cyclization. The details of the 1,5-proton transfer reaction were elucidated using methanol-O-d and the collapse preferences and intramolecularity in this medium were determined.

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