Bibliographic Citation
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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 Date | 1979 Feb 01 |
OSTI Identifier | OSTI ID: 6872434 |
Report Number(s) | CONF-790415- |
Other Number(s) | CODEN: ACPCA |
Resource Type | Conference |
Specific Type | Journal Article |
Resource Relation | Am. 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 Org | I.B.M. Res. Lab. |
Subject | 400301 -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987); ;ALKYNES-- CHEMICAL PREPARATION;ALKYNES-- ISOMERIZATION;AMIDES-- CATALYTIC EFFECTS;POTASSIUM COMPOUNDS-- CATALYTIC EFFECTS; ISOTOPIC EXCHANGE;PROTON REACTIONS |
Related Subject | ALKALI 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 Publication | United States |
Language | English |
Format | Pages: 219-225 |
System Entry Date | 2001 May 13 |
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