A Novel Nucleophilic Substitution of in Situ Generated 3-tert-Butyldimethyl- silyloxyalk-2-enylsulfonium Salts with Allylindium Reagents

2001 ◽  
Vol 3 (20) ◽  
pp. 3205-3207 ◽  
Author(s):  
Phil Ho Lee ◽  
Kooyeon Lee ◽  
Sunggak Kim
Keyword(s):  
Nucleophilic Substitution

scholarly journals Intramolecular nucleophilic addition of carbanions generated from N-benzylamides to cyclopropenes

2018 ◽  
Vol 16 (2) ◽  
pp. 285-294 ◽  
Author(s):  
Vladimir Maslivetc ◽  
Colby Barrett ◽  
Nicolai A. Aksenov ◽  
Marina Rubina ◽  
Michael Rubin
Keyword(s):  
Nucleophilic Substitution ◽  
Nucleophilic Addition ◽  
Unusual Reaction ◽  
Intramolecular Nucleophilic Substitution ◽  
Facile Preparation ◽  
Nitrogen Ylides

An unusual reaction is described, involving a formal intramolecular nucleophilic substitution of bromocyclopropanes with nitrogen ylides generated in situ from N-benzyl carboxamides. This reaction involves cyclopropene intermediates and allows for the facile preparation of 3-azabicyclo[3.1.0]hexan-2-ones.

scholarly journals Fluorine effect in nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-β-D-hexopyranose

2020 ◽  
Vol 16 ◽  
pp. 2880-2887
Author(s):  
Danny Lainé ◽  
Vincent Denavit ◽  
Olivier Lessard ◽  
Laurie Carrier ◽  
Charles-Émile Fecteau ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Fluorine Atom ◽  
Synthetic Approach ◽  
Nucleophilic Fluorination

In this work, we have developed a simple synthetic approach using Et3N·3HF as an alternative to the DAST reagent. We controlled the stereochemistry of the nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-4-O-triflate-β-ᴅ-talopyranose using Et3N·3HF or in situ generated Et3N·1HF. The influence of the fluorine atom at C2 on reactivity at C4 could contribute to a new fluorine effect in nucleophilic substitution. Finally, with the continuous objective of synthesizing novel multi-vicinal fluorosugars, we prepared one difluorinated and one trifluorinated alditol analogue.

Reaction of Ethyl 5-Substituted-2-furoylmalonates with Secondary Amines

1994 ◽  
Vol 59 (6) ◽  
pp. 1400-1407 ◽  
Author(s):  
Rudolf Kada ◽  
Jarmila Bruncková ◽  
Pavol Bobál'
Keyword(s):  
Nucleophilic Substitution ◽  
Secondary Amines ◽  
Ethyl Malonate ◽  
Magnesium Salts

In situ prepared magnesium salts of ethyl malonate react with 5-X-2-furoyl chlorides (X = Br, NO2, C6H5S and C6H5SO2) to give the corresponding ethyl 5-X-2-furoylmalonates. On treatment of these compounds with secondary amines no nucleophilic substitution of the group X in position 5 of the furan nucleus took place but, instead, amides of 5-X-2-furancarboxylic acids were isolated.

Synthesis of (benzenesulfonyl)difluoromethyl thioethers from ((difluoromethyl)sulfonyl)benzene and organothiocyanates generated in situ

2021 ◽  
Author(s):  
Cheng Wu ◽  
Xiao Shen ◽  
Jian-Jun Dai ◽  
Jun Xu ◽  
Hua-Jian Xu
Keyword(s):  
Transition Metal ◽  
Nucleophilic Substitution ◽  
Metal Free

Easily available aryl and alkyl thiocyanates were converted into the corresponding (benzenesulfonyl)difluoromethyl thioethers via direct nucleophilic substitution of ((difluoromethyl)-sulfonyl)benzene under transition metal free conditions. Combined with various thiocyanation methods, this...

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