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Title: New approaches to the preparation and transformation of acetylenic compounds via KAPA potassium 3-aminopropylamide superbase chemistry

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.

Authors:
Publication Date:
Research Org.:
I.B.M. Res. Lab.
OSTI Identifier:
6872434
Alternate Identifier(s):
OSTI ID: 6872434
Report Number(s):
CONF-790415-
Journal ID: CODEN: ACPCA
Resource Type:
Conference
Journal Name:
Am. Chem. Soc., Div. Pet. Chem., Prepr.; (United States)
Additional Journal Information:
Journal Volume: 24:1; Conference: 177. national meeting of the American Chemical Society, Honolulu, HI, USA, 1 Apr 1979
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; ALKYNES; CHEMICAL PREPARATION; ISOMERIZATION; AMIDES; CATALYTIC EFFECTS; POTASSIUM COMPOUNDS; ISOTOPIC EXCHANGE; PROTON REACTIONS; ALKALI METAL COMPOUNDS; BARYON REACTIONS; CHARGED-PARTICLE REACTIONS; CHEMICAL REACTIONS; HADRON REACTIONS; HYDROCARBONS; NUCLEAR REACTIONS; NUCLEON REACTIONS; ORGANIC COMPOUNDS; ORGANIC NITROGEN COMPOUNDS; SYNTHESIS 400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)

Citation Formats

Brown, C.A. New approaches to the preparation and transformation of acetylenic compounds via KAPA potassium 3-aminopropylamide superbase chemistry. United States: N. p., 1979. Web.
Brown, C.A. New approaches to the preparation and transformation of acetylenic compounds via KAPA potassium 3-aminopropylamide superbase chemistry. United States.
Brown, C.A. Thu . "New approaches to the preparation and transformation of acetylenic compounds via KAPA potassium 3-aminopropylamide superbase chemistry". United States.
@article{osti_6872434,
title = {New approaches to the preparation and transformation of acetylenic compounds via KAPA potassium 3-aminopropylamide superbase chemistry},
author = {Brown, C.A.},
abstractNote = {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.},
doi = {},
journal = {Am. Chem. Soc., Div. Pet. Chem., Prepr.; (United States)},
number = ,
volume = 24:1,
place = {United States},
year = {1979},
month = {2}
}

Conference:
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