Tricarbonyl(dihydroazepinyl)chromium complexes and methylenepyrrolidines from (2'-dimethylaminoethenyl)carbenechromium complexes

Heiko Schirmer; Thomas Labahn; Bernard Flynn; Yao Ting Wu; Armin De Meijere

doi:10.1055/s-1999-2960

Tricarbonyl(dihydroazepinyl)chromium complexes and methylenepyrrolidines from (2'-dimethylaminoethenyl)carbenechromium complexes

Heiko Schirmer, Thomas Labahn, Bernard Flynn, Yao Ting Wu, Armin De Meijere^*

^*Corresponding author for this work

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

15 Citations (Scopus)

Abstract

The (3-amino-1-ethoxyalkenylidene)pentacarbonylchromium complexes 1 and 8 react with bulkily substituted terminal alkynes 2 and 9 in tetrahydrofuran to give η⁵-tricarbonyl(dihydroazepinyl)chromium complexes 3 and 12a which can be isolated in low yields. When the reactions are carried out in pyridine, the formal [5+2] cycloaddition is favored, but the complexes of type 12 are immediately further transformed to 2- (isobutyrylmethylene)pyrrolidines 13 in good yields.

Original language	English
Pages (from-to)	2004-2006
Number of pages	3
Journal	Synlett
Issue number	12
DOIs	https://doi.org/10.1055/s-1999-2960
Publication status	Published - 1999

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title = "Tricarbonyl(dihydroazepinyl)chromium complexes and methylenepyrrolidines from (2'-dimethylaminoethenyl)carbenechromium complexes",

abstract = "The (3-amino-1-ethoxyalkenylidene)pentacarbonylchromium complexes 1 and 8 react with bulkily substituted terminal alkynes 2 and 9 in tetrahydrofuran to give η5-tricarbonyl(dihydroazepinyl)chromium complexes 3 and 12a which can be isolated in low yields. When the reactions are carried out in pyridine, the formal [5+2] cycloaddition is favored, but the complexes of type 12 are immediately further transformed to 2- (isobutyrylmethylene)pyrrolidines 13 in good yields.",

keywords = "Alkynes, Carbene complexes, Methylenepyrrolidines, Tricarbonyl(dihydroazepinyl)chromium complexes",

author = "Heiko Schirmer and Thomas Labahn and Bernard Flynn and Wu, \{Yao Ting\} and \{De Meijere\}, Armin",

year = "1999",

doi = "10.1055/s-1999-2960",

language = "English",

pages = "2004--2006",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "12",

}

TY - JOUR

T1 - Tricarbonyl(dihydroazepinyl)chromium complexes and methylenepyrrolidines from (2'-dimethylaminoethenyl)carbenechromium complexes

AU - Schirmer, Heiko

AU - Labahn, Thomas

AU - Flynn, Bernard

AU - Wu, Yao Ting

AU - De Meijere, Armin

PY - 1999

Y1 - 1999

N2 - The (3-amino-1-ethoxyalkenylidene)pentacarbonylchromium complexes 1 and 8 react with bulkily substituted terminal alkynes 2 and 9 in tetrahydrofuran to give η5-tricarbonyl(dihydroazepinyl)chromium complexes 3 and 12a which can be isolated in low yields. When the reactions are carried out in pyridine, the formal [5+2] cycloaddition is favored, but the complexes of type 12 are immediately further transformed to 2- (isobutyrylmethylene)pyrrolidines 13 in good yields.

AB - The (3-amino-1-ethoxyalkenylidene)pentacarbonylchromium complexes 1 and 8 react with bulkily substituted terminal alkynes 2 and 9 in tetrahydrofuran to give η5-tricarbonyl(dihydroazepinyl)chromium complexes 3 and 12a which can be isolated in low yields. When the reactions are carried out in pyridine, the formal [5+2] cycloaddition is favored, but the complexes of type 12 are immediately further transformed to 2- (isobutyrylmethylene)pyrrolidines 13 in good yields.

KW - Alkynes

KW - Carbene complexes

KW - Methylenepyrrolidines

KW - Tricarbonyl(dihydroazepinyl)chromium complexes

UR - https://www.scopus.com/pages/publications/0032757235

U2 - 10.1055/s-1999-2960

DO - 10.1055/s-1999-2960

M3 - Article

SN - 0936-5214

SP - 2004

EP - 2006

JO - Synlett

JF - Synlett

IS - 12

ER -

Tricarbonyl(dihydroazepinyl)chromium complexes and methylenepyrrolidines from (2'-dimethylaminoethenyl)carbenechromium complexes

Abstract

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