The synthesis and characterization of 1-formyl-2-acylcyclopentadienylthallium compounds

Mark T. Blankenbuehler; John P. Selegue

doi:10.1016/S0022-328X(01)01185-8

The synthesis and characterization of 1-formyl-2-acylcyclopentadienylthallium compounds

Mark T. Blankenbuehler
, John P. Selegue

Producción científica: Article › revisión exhaustiva

12 Citas (Scopus)

Resumen

The reaction of sodium cyclopentadienide with RCOOEt (R=Me, Ph, 2-thienyl, or OEt) or Bu^tCOCl followed by Vilsmeier reagent in the presence of excess sodium methoxide produces the 2-substituted-6-dimethylaminofulvenes 1a-e in modest yields. Basic hydrolysis results in the formation of 2-substituted-6-hydroxyfulvenes 2a-e in very good yields. Subsequent deprotonation with TlOEt yields the 1-formyl-2-acyl or carboethoxy cyclopentadienylthallium compounds 3a-e.

Idioma original	English
Páginas (desde-hasta)	268-274
Número de páginas	7
Publicación	Journal of Organometallic Chemistry
Volumen	642
N.º	1-2
DOI	https://doi.org/10.1016/S0022-328X(01)01185-8
Estado	Published - 2002

Nota bibliográfica

Funding Information:
We thank the National Science Foundation (EPSCoR EPS-9452895 and MRSEC DMR-9809686) and the US Department of Energy (DE-FG02-00ER45847 and subcontract 10186-00-23) for support of this research.

Financiación

We thank the National Science Foundation (EPSCoR EPS-9452895 and MRSEC DMR-9809686) and the US Department of Energy (DE-FG02-00ER45847 and subcontract 10186-00-23) for support of this research.

Financiadores	Número del financiador
US Department of Energy	DE-FG02-00ER45847, 10186-00-23
National Science Foundation (NSF)
Office of Experimental Program to Stimulate Competitive Research	MRSEC DMR-9809686, EPS-9452895

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/S0022-328X(01)01185-8

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title = "The synthesis and characterization of 1-formyl-2-acylcyclopentadienylthallium compounds",

abstract = "The reaction of sodium cyclopentadienide with RCOOEt (R=Me, Ph, 2-thienyl, or OEt) or ButCOCl followed by Vilsmeier reagent in the presence of excess sodium methoxide produces the 2-substituted-6-dimethylaminofulvenes 1a-e in modest yields. Basic hydrolysis results in the formation of 2-substituted-6-hydroxyfulvenes 2a-e in very good yields. Subsequent deprotonation with TlOEt yields the 1-formyl-2-acyl or carboethoxy cyclopentadienylthallium compounds 3a-e.",

keywords = "Acyl, Carboethoxy, Cyclopentadienide, Formyl, Thallium, Vilsmeier",

author = "Blankenbuehler, \{Mark T.\} and Selegue, \{John P.\}",

note = "Funding Information: We thank the National Science Foundation (EPSCoR EPS-9452895 and MRSEC DMR-9809686) and the US Department of Energy (DE-FG02-00ER45847 and subcontract 10186-00-23) for support of this research.",

year = "2002",

doi = "10.1016/S0022-328X(01)01185-8",

language = "English",

volume = "642",

pages = "268--274",

number = "1-2",

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TY - JOUR

T1 - The synthesis and characterization of 1-formyl-2-acylcyclopentadienylthallium compounds

AU - Blankenbuehler, Mark T.

AU - Selegue, John P.

N1 - Funding Information: We thank the National Science Foundation (EPSCoR EPS-9452895 and MRSEC DMR-9809686) and the US Department of Energy (DE-FG02-00ER45847 and subcontract 10186-00-23) for support of this research.

PY - 2002

Y1 - 2002

N2 - The reaction of sodium cyclopentadienide with RCOOEt (R=Me, Ph, 2-thienyl, or OEt) or ButCOCl followed by Vilsmeier reagent in the presence of excess sodium methoxide produces the 2-substituted-6-dimethylaminofulvenes 1a-e in modest yields. Basic hydrolysis results in the formation of 2-substituted-6-hydroxyfulvenes 2a-e in very good yields. Subsequent deprotonation with TlOEt yields the 1-formyl-2-acyl or carboethoxy cyclopentadienylthallium compounds 3a-e.

AB - The reaction of sodium cyclopentadienide with RCOOEt (R=Me, Ph, 2-thienyl, or OEt) or ButCOCl followed by Vilsmeier reagent in the presence of excess sodium methoxide produces the 2-substituted-6-dimethylaminofulvenes 1a-e in modest yields. Basic hydrolysis results in the formation of 2-substituted-6-hydroxyfulvenes 2a-e in very good yields. Subsequent deprotonation with TlOEt yields the 1-formyl-2-acyl or carboethoxy cyclopentadienylthallium compounds 3a-e.

KW - Acyl

KW - Carboethoxy

KW - Cyclopentadienide

KW - Formyl

KW - Thallium

KW - Vilsmeier

UR - https://www.scopus.com/pages/publications/27544496342

UR - https://www.scopus.com/pages/publications/27544496342#tab=citedBy

U2 - 10.1016/S0022-328X(01)01185-8

DO - 10.1016/S0022-328X(01)01185-8

M3 - Article

AN - SCOPUS:27544496342

SN - 0022-328X

VL - 642

SP - 268

EP - 274

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

IS - 1-2

ER -

The synthesis and characterization of 1-formyl-2-acylcyclopentadienylthallium compounds

Resumen

Nota bibliográfica

Financiación

ASJC Scopus subject areas

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