Synthesis of Thio-Linked Disaccharides by 1→2 Intramolecular Thioglycosyl Migration:  Oxacarbenium versus Episulfonium Ion Intermediates

2000 ◽  
Vol 65 (15) ◽  
pp. 4607-4617 ◽  
Author(s):  
Blair D. Johnston ◽  
B. Mario Pinto
Keyword(s):  
Episulfonium Ion

Role for an episulfonium ion in S-(2-chloroethyl)-DL-cysteine-induced cytotoxicity and its reaction with glutathione

Biochemistry ◽  
1987 ◽  
Vol 26 (11) ◽  
pp. 3017-3023 ◽  
Author(s):  
William W. Webb ◽  
Adnan A. Elfarra ◽  
Kathy D. Webster ◽  
Rebecca E. Thom ◽  
M. W. Anders
Keyword(s):  
Episulfonium Ion

An episulfonium ion mediated ring expansion of 1-alkenylcycloakanols

1989 ◽  
Vol 30 (45) ◽  
pp. 6181-6184 ◽  
Author(s):  
Sunggak Kim ◽  
Jung Ho Park
Keyword(s):  
Ring Expansion ◽  
Episulfonium Ion

Novel Stereoselective Synthesis of b-Lactams via Episulfonium Ion Intermediate

Heterocycles ◽  
1982 ◽  
Vol 19 (8) ◽  
pp. 1435 ◽  
Author(s):  
Tetsuji Kametani ◽  
Masataka Ihara ◽  
Keiichiro Fukumoto
Keyword(s):  
Stereoselective Synthesis ◽  
Episulfonium Ion

Cyclic ether synthesis: sulfenyletherification with benzenesulfenyl chloride/N, N-diisopropylethylamine and sulfenate ester cycloadditions

1987 ◽  
Vol 65 (8) ◽  
pp. 1833-1837 ◽  
Author(s):  
Sudersan M. Tuladhar ◽  
Alex G. Fallis
Keyword(s):  
Cyclic Ether ◽  
Cyclic Ethers ◽  
Nucleophilic Displacement ◽  
Ether Synthesis ◽  
Special Case ◽  
General Method ◽  
Episulfonium Ion

A general method for the formation of the cyclic ethers 9, 10, 13, 14, 16, and 28 and the lactone 30 is described. The procedure employs benzenesulfenyl chloride prepared insitu in acetonitrile and N,N-diisopropylethylamine to generate a thiiranium (episulfonium) ion intermediate from which the cyclic products arise by internal nucleophilic displacement. In the special case of the norbornene alcohols 1 and 2 the oxetanes 5 and 6 are formed by intramolecular sulfenate ester cycloaddition.

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