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Title New approaches to the preparation and transformation of acetylenic compounds via KAPA potassium 3-aminopropylamide superbase chemistry
Creator/Author Brown, C.A.
Publication Date1979 Feb 01
OSTI IdentifierOSTI ID: 6872434
Report Number(s)CONF-790415-
Other Number(s)CODEN: ACPCA
Resource TypeConference
Specific TypeJournal Article
Resource RelationAm. Chem. Soc., Div. Pet. Chem., Prepr. ; Vol/Issue: 24:1; 177. national meeting of the American Chemical Society; 1 Apr 1979; Honolulu, HI, USA
Research OrgI.B.M. Res. Lab.
Subject400301 -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987); ;ALKYNES-- CHEMICAL PREPARATION;ALKYNES-- ISOMERIZATION;AMIDES-- CATALYTIC EFFECTS;POTASSIUM COMPOUNDS-- CATALYTIC EFFECTS; ISOTOPIC EXCHANGE;PROTON REACTIONS
Related SubjectALKALI METAL COMPOUNDS;BARYON REACTIONS;CHARGED-PARTICLE REACTIONS;CHEMICAL REACTIONS;HADRON REACTIONS;HYDROCARBONS;NUCLEAR REACTIONS;NUCLEON REACTIONS;ORGANIC COMPOUNDS;ORGANIC NITROGEN COMPOUNDS;SYNTHESIS
Description/Abstract KAPA is a new alkamide superbase which is readily prepared from potassium hydride and 3-aminopropylamine and used in solutions of the excess amine, and which shows exceptional activity for base-catalyzed reactions involving proton abstraction, such as olefin and acetylene isomerization, aryl carbon-hydrogen isotopic exchange, and elimination.^Thus, 3-hexyne is converted by KAPA at 0/sup 0/C to potassium 1-hexynide, which is then hydrolyzed to 1-hexyne in 96Vertical Bar3< yield.^Alkynes with longer chains such as 4-octyne, 7-tetradecyne, and methylnonynes, readily undergo triple-bond migration to the chain terminus via the rapid and mild ``acetylene zipper`` isomerization.
Country of PublicationUnited States
LanguageEnglish
FormatPages: 219-225
System Entry Date2001 May 13

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