1,4-diazabicyclo[2.2.2]octane-catalyzed self- and cross- condensation of α-acetylenic ketones

P. Veeraraghavan Ramachandran; Michael T. Rudd; M. Venkat Ram Reddy

doi:10.1016/S0040-4039(99)00630-9

1,4-diazabicyclo[2.2.2]octane-catalyzed self- and cross- condensation of α-acetylenic ketones

P. Veeraraghavan Ramachandran
, Michael T. Rudd
, M. Venkat Ram Reddy

Chemistry & Biochemistry

Research output: Contribution to journal › Article › peer-review

26 Scopus citations

Abstract

3-Butyn-2-one condenses with itself in the presence of 0.1 molar equiv of Dabco providing 80% yield of E-3-(1-buten-3-yn-2-oxy)-buten-2-one. Substitution at the acetylene terminus prevents the condensation. However, such ketones can be condensed with terminal acetylenic ketones to provide the cross-coupled products in high yields.

Original language	English (US)
Pages (from-to)	3819-3822
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	20
DOIs	https://doi.org/10.1016/S0040-4039(99)00630-9
State	Published - May 14 1999

Bibliographical note

Funding Information:
The financial assistance from the Purdue Borane Research Fund is gratefully

Keywords

Condensation
Dabco
Divinyl ether
Trialkylamine
α-acetylenic ketones

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10.1016/S0040-4039(99)00630-9

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title = "1,4-diazabicyclo[2.2.2]octane-catalyzed self- and cross- condensation of α-acetylenic ketones",

abstract = "3-Butyn-2-one condenses with itself in the presence of 0.1 molar equiv of Dabco providing 80\% yield of E-3-(1-buten-3-yn-2-oxy)-buten-2-one. Substitution at the acetylene terminus prevents the condensation. However, such ketones can be condensed with terminal acetylenic ketones to provide the cross-coupled products in high yields.",

keywords = "Condensation, Dabco, Divinyl ether, Trialkylamine, α-acetylenic ketones",

author = "Ramachandran, \{P. Veeraraghavan\} and Rudd, \{Michael T.\} and Reddy, \{M. Venkat Ram\}",

note = "Funding Information: The financial assistance from the Purdue Borane Research Fund is gratefully",

year = "1999",

month = may,

day = "14",

doi = "10.1016/S0040-4039(99)00630-9",

language = "English (US)",

volume = "40",

pages = "3819--3822",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - 1,4-diazabicyclo[2.2.2]octane-catalyzed self- and cross- condensation of α-acetylenic ketones

AU - Ramachandran, P. Veeraraghavan

AU - Rudd, Michael T.

AU - Reddy, M. Venkat Ram

N1 - Funding Information: The financial assistance from the Purdue Borane Research Fund is gratefully

PY - 1999/5/14

Y1 - 1999/5/14

N2 - 3-Butyn-2-one condenses with itself in the presence of 0.1 molar equiv of Dabco providing 80% yield of E-3-(1-buten-3-yn-2-oxy)-buten-2-one. Substitution at the acetylene terminus prevents the condensation. However, such ketones can be condensed with terminal acetylenic ketones to provide the cross-coupled products in high yields.

AB - 3-Butyn-2-one condenses with itself in the presence of 0.1 molar equiv of Dabco providing 80% yield of E-3-(1-buten-3-yn-2-oxy)-buten-2-one. Substitution at the acetylene terminus prevents the condensation. However, such ketones can be condensed with terminal acetylenic ketones to provide the cross-coupled products in high yields.

KW - Condensation

KW - Dabco

KW - Divinyl ether

KW - Trialkylamine

KW - α-acetylenic ketones

UR - https://www.scopus.com/pages/publications/0033553441

UR - https://www.scopus.com/pages/publications/0033553441#tab=citedBy

U2 - 10.1016/S0040-4039(99)00630-9

DO - 10.1016/S0040-4039(99)00630-9

M3 - Article

AN - SCOPUS:0033553441

SN - 0040-4039

VL - 40

SP - 3819

EP - 3822

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 20

ER -

1,4-diazabicyclo[2.2.2]octane-catalyzed self- and cross- condensation of α-acetylenic ketones

Abstract

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Keywords

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