An efficient three-step synthesis of cyclopenta[b]pyrans via 2-donor-substituted fischer ethenylcarbenechromium complexes

Armin De Meijere; Heiko Schirmer; Frank Stein; Frank Funke; Michael Duetsch; Yao Ting Wu; Mathias Noltemeyer; Thomas Belgardt; Burkhard Knieriem

doi:10.1002/chem.200500043

An efficient three-step synthesis of cyclopenta[b]pyrans via 2-donor-substituted fischer ethenylcarbenechromium complexes

Armin De Meijere, Heiko Schirmer, Frank Stein, Frank Funke, Michael Duetsch, Yao Ting Wu, Mathias Noltemeyer, Thomas Belgardt, Burkhard Knieriem

Department of Chemistry

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

13 Citations (Scopus)

Abstract

A wide range of cyclopenta[b]pyrans 4 has been synthesized in a one-pot reaction by treatment of different 2-donorsubstituted ethenylcarbenechromium complexes 2 with alkynes in THF in moderate to excellent yields (41-90% for 14 out of 25 examples). The starting materials 2 are readily available in good to excellent yields (76-99% for 25 out of 36 examples) by Michael addition of amines, alcohols and thiols, respectively, to the corresponding alkynylcarbenechromium complexes 1. Due to their 10 π-electrons in a cross-conjugated bicyclic system, cyclopenta[b]pyrans have been termed pseudoazulenes, as they indeed have similar UV/Vis-spectroscopic properties.

Original language	English
Pages (from-to)	4132-4148
Number of pages	17
Journal	Chemistry - A European Journal
Volume	11
Issue number	14
DOIs	https://doi.org/10.1002/chem.200500043
Publication status	Published - 2005 Jul 4

All Science Journal Classification (ASJC) codes

Catalysis
Organic Chemistry

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title = "An efficient three-step synthesis of cyclopenta[b]pyrans via 2-donor-substituted fischer ethenylcarbenechromium complexes",

abstract = "A wide range of cyclopenta[b]pyrans 4 has been synthesized in a one-pot reaction by treatment of different 2-donorsubstituted ethenylcarbenechromium complexes 2 with alkynes in THF in moderate to excellent yields (41-90% for 14 out of 25 examples). The starting materials 2 are readily available in good to excellent yields (76-99% for 25 out of 36 examples) by Michael addition of amines, alcohols and thiols, respectively, to the corresponding alkynylcarbenechromium complexes 1. Due to their 10 π-electrons in a cross-conjugated bicyclic system, cyclopenta[b]pyrans have been termed pseudoazulenes, as they indeed have similar UV/Vis-spectroscopic properties.",

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An efficient three-step synthesis of cyclopenta[b]pyrans via 2-donor-substituted fischer ethenylcarbenechromium complexes. / De Meijere, Armin; Schirmer, Heiko; Stein, Frank; Funke, Frank; Duetsch, Michael; Wu, Yao Ting; Noltemeyer, Mathias; Belgardt, Thomas; Knieriem, Burkhard.

In: Chemistry - A European Journal, Vol. 11, No. 14, 04.07.2005, p. 4132-4148.

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

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AU - De Meijere, Armin

AU - Schirmer, Heiko

AU - Stein, Frank

AU - Funke, Frank

AU - Duetsch, Michael

AU - Wu, Yao Ting

AU - Noltemeyer, Mathias

AU - Belgardt, Thomas

AU - Knieriem, Burkhard

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An efficient three-step synthesis of cyclopenta[b]pyrans via 2-donor-substituted fischer ethenylcarbenechromium complexes

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