Preparative nucleophilic substitution with "betylates". Substrate phase transfer and substrate-reagent ion-pair reactions

1978 ◽  
Vol 100 (5) ◽  
pp. 1637-1639 ◽  
Author(s):  
J. F. King ◽  
S. M. Loosmore ◽  
J. D. Lock ◽  
M. Aslam
Keyword(s):  
Nucleophilic Substitution ◽  
Phase Transfer ◽  
Ion Pair

Betylates. 4. The synthesis and preparative nucleophilic substitution reactions of alkyl S-[3]betylates

1983 ◽  
Vol 61 (2) ◽  
pp. 235-243 ◽  
Author(s):  
James Frederick King ◽  
Stanislaw Skonieczny ◽  
Gary Allan Poole
Keyword(s):  
Nucleophilic Substitution ◽  
Phase Transfer ◽  
Ion Pair ◽  
Substitution Reactions ◽  
Nucleophilic Substitution Reactions ◽  
Transfer Processes ◽  
Nitrogen Analogues

Alkyl S-[3]betylates (S,S-dialkyl-S-3[(alkyloxy)sulfonyl]propylsulfonium salts), the first examples of S-betylates (sulfonioalkanesulfonic esters), have been synthesized by two routes, and their suitability as intermediates in the transformation of alcohols by nucleophilic substitution reactions examined. They have been found to react readily in stoichiometric phase transfer processes, including substrate–reagent ion-pair reactions, like their previously studied nitrogen analogues, with the following particular features: (a) they may be used with basic nucleophiles (unlike [2]betylates), (b) they are more simply made from commercially available starting materials than [3]betylates, and (c) they can be made by a route that avoids a final alkylation step.

Phase-Transfer Mediated Heteroaromatic Nucleophilic Substitution: Introduction of a β-Adrenergic Blocking Moiety

Synthesis ◽  
1980 ◽  
Vol 1980 (07) ◽  
pp. 573-575 ◽  
Author(s):  
Angelina J. Serio Duggan ◽  
Edward J. J. Grabowski ◽  
Warren K. Russ
Keyword(s):  
Nucleophilic Substitution ◽  
Phase Transfer ◽  
Adrenergic Blocking
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