Reversal of Polarity by Catalytic SET Oxidation: Synthesis of Azabicyclo[m.n.o]alkanes via Chemoselective Reduction of Amidines

Author(s):  
Sundarababu Baskaran ◽  
Kirana D V ◽  
Kanak Kanti Das

A one-pot catalytic method has been developed for the stereoselective synthesis of cyclopropane-fused cyclic amidines using CuBr2/K2S2O8 as an efficient single electron transfer (SET) oxidative system. The generality of this...

1995 ◽  
Vol 73 (3) ◽  
pp. 444-452 ◽  
Author(s):  
James Clayton Baum ◽  
Bradley Eugene Black ◽  
Laura Precedo ◽  
John Edward Goehl ◽  
Richard Francis Langler

The one-pot conversion of a mercaptan and an aryl methanesulfonate into a trithioorthoformate is described. The intermediacy of a sulfide-sulfonate ester is firmly established. Experimental and computational results permit the formulation of a possible pathway for the formation of the intermediate sulfide-sulfonate ester. Keywords: single electron transfer, sulfonate esters, sulfide-sulfonate esters.


1996 ◽  
Vol 74 (9) ◽  
pp. 1638-1648 ◽  
Author(s):  
Kashyapa Ananda Ginige ◽  
John Edward Goehl ◽  
Richard Francis Langler

A previous report has established the intermediacy of a sulfide-sulfonate ester in the one-pot conversion of an aryl mercaptan and a sulfonate ester into the corresponding trithioorthoformate. This report describes evidence for the sequential intermediacy of a bissulfide-sulfonate ester and a dithiosulfène in the conversion of the sulfide-sulfonate ester into the trithioorthoformate. A new sulfonate ester is shown to give the highest yield of trithioorthoformate. Key words: single electron transfer, sulfonate esters, sulfenes.


RSC Advances ◽  
2020 ◽  
Vol 10 (49) ◽  
pp. 29373-29377
Author(s):  
Hikari Okita ◽  
Yuna Kato ◽  
Tatsuki Masuzawa ◽  
Kosuke Arai ◽  
Sayuri Takeo ◽  
...  

An efficient synthesis of Gly-Gly-type (E)-methylalkene and (Z)-chloroalkene dipeptide isosteres is realized by organocuprate-mediated single electron transfer reduction.


Synthesis ◽  
2021 ◽  
Author(s):  
Pengkai Wang ◽  
yan xu cao ◽  
Songlin Zhang

The utilities of ytterbium(II) reagent, both as nucleophilic reagent and single electron transfer reagent in the reaction of isatin derivatives with ytterbium(II) reagent are reported for the first time in this paper. From a synthetic point of view, a general, efficient, and experimentally simple one-pot method for preparation of 3-substituted-2-oxindoles was developed.


2016 ◽  
Vol 14 (48) ◽  
pp. 11415-11425 ◽  
Author(s):  
Gullapalli Kumaraswamy ◽  
Swargam Vijaykumar ◽  
Kukkadapu Ankamma ◽  
Vykunthapu Narayanarao

The stereoselective synthesis of α-phenylselenyl- or telluryl β-aryl acrylaldehydes/ketones from aryl allenes/1,3-diarylallene by an oxidative photo-induced single electron transfer process using benign ambient air as a sole oxidant was achieved.


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