Preparation, structure and reactivity of aminocarbene complexes of chromium and molybdenum derived from primary amines

B. Denise, P. Dubost, A. Parlier, M. Rudler, H. Rudler, J. C. Daran, J. Vaissermann, F. Delgado, A. R. Arevalo, R. A. Toscano, C. Alvarez

Research output: Contribution to journalArticle

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Abstract

The synthesis and reactivity towards diphenylacetylene of a series of aminocarbene complexes of general structure (CO)5MC(NHR′)R (M = Cr, R = CH3, Ph, R' = cyclohexyl, cyclopropyl, benzyl) are described: they lead by alkyne insertion followed by a 1,4 hydrogen shift, to imine complexes, which, upon hydrolysis, give the corresponding ketones. When R′CH2Ph, along with the expected imine, a tetraphenylcyclopentadiene resulting from the coupling of two PhCCPh and of a carbene moiety, is formed; its structure has been determined by an X-ray study. In the case of aminopyridine, bidentate carbene complexes (the structure of which was confirmed by an X-ray study of (CO)4CrC (CH3)NHNC5H5) are formed, and these also react with PhCCPh to give for M = Mo, new pyrrolinones through alkyne/CO insertion followed by a 1,2 hydrogen shift. © 1991.
Original languageAmerican English
Pages (from-to)377-393
Number of pages337
JournalJournal of Organometallic Chemistry
DOIs
StatePublished - 5 Nov 1991
Externally publishedYes

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Molybdenum
carbenes
Chromium
alkynes
Carbon Monoxide
imines
molybdenum
Amines
insertion
chromium
amines
Imines
Alkynes
reactivity
X rays
Hydrogen
preparation
shift
hydrogen
Ketones

Cite this

Denise, B. ; Dubost, P. ; Parlier, A. ; Rudler, M. ; Rudler, H. ; Daran, J. C. ; Vaissermann, J. ; Delgado, F. ; Arevalo, A. R. ; Toscano, R. A. ; Alvarez, C. / Preparation, structure and reactivity of aminocarbene complexes of chromium and molybdenum derived from primary amines. In: Journal of Organometallic Chemistry. 1991 ; pp. 377-393.
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abstract = "The synthesis and reactivity towards diphenylacetylene of a series of aminocarbene complexes of general structure (CO)5MC(NHR′)R (M = Cr, R = CH3, Ph, R' = cyclohexyl, cyclopropyl, benzyl) are described: they lead by alkyne insertion followed by a 1,4 hydrogen shift, to imine complexes, which, upon hydrolysis, give the corresponding ketones. When R′CH2Ph, along with the expected imine, a tetraphenylcyclopentadiene resulting from the coupling of two PhCCPh and of a carbene moiety, is formed; its structure has been determined by an X-ray study. In the case of aminopyridine, bidentate carbene complexes (the structure of which was confirmed by an X-ray study of (CO)4CrC (CH3)NHNC5H5) are formed, and these also react with PhCCPh to give for M = Mo, new pyrrolinones through alkyne/CO insertion followed by a 1,2 hydrogen shift. {\circledC} 1991.",
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Denise, B, Dubost, P, Parlier, A, Rudler, M, Rudler, H, Daran, JC, Vaissermann, J, Delgado, F, Arevalo, AR, Toscano, RA & Alvarez, C 1991, 'Preparation, structure and reactivity of aminocarbene complexes of chromium and molybdenum derived from primary amines', Journal of Organometallic Chemistry, pp. 377-393. https://doi.org/10.1016/0022-328X(91)80223-7

Preparation, structure and reactivity of aminocarbene complexes of chromium and molybdenum derived from primary amines. / Denise, B.; Dubost, P.; Parlier, A.; Rudler, M.; Rudler, H.; Daran, J. C.; Vaissermann, J.; Delgado, F.; Arevalo, A. R.; Toscano, R. A.; Alvarez, C.

In: Journal of Organometallic Chemistry, 05.11.1991, p. 377-393.

Research output: Contribution to journalArticle

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AU - Denise, B.

AU - Dubost, P.

AU - Parlier, A.

AU - Rudler, M.

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AU - Daran, J. C.

AU - Vaissermann, J.

AU - Delgado, F.

AU - Arevalo, A. R.

AU - Toscano, R. A.

AU - Alvarez, C.

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N2 - The synthesis and reactivity towards diphenylacetylene of a series of aminocarbene complexes of general structure (CO)5MC(NHR′)R (M = Cr, R = CH3, Ph, R' = cyclohexyl, cyclopropyl, benzyl) are described: they lead by alkyne insertion followed by a 1,4 hydrogen shift, to imine complexes, which, upon hydrolysis, give the corresponding ketones. When R′CH2Ph, along with the expected imine, a tetraphenylcyclopentadiene resulting from the coupling of two PhCCPh and of a carbene moiety, is formed; its structure has been determined by an X-ray study. In the case of aminopyridine, bidentate carbene complexes (the structure of which was confirmed by an X-ray study of (CO)4CrC (CH3)NHNC5H5) are formed, and these also react with PhCCPh to give for M = Mo, new pyrrolinones through alkyne/CO insertion followed by a 1,2 hydrogen shift. © 1991.

AB - The synthesis and reactivity towards diphenylacetylene of a series of aminocarbene complexes of general structure (CO)5MC(NHR′)R (M = Cr, R = CH3, Ph, R' = cyclohexyl, cyclopropyl, benzyl) are described: they lead by alkyne insertion followed by a 1,4 hydrogen shift, to imine complexes, which, upon hydrolysis, give the corresponding ketones. When R′CH2Ph, along with the expected imine, a tetraphenylcyclopentadiene resulting from the coupling of two PhCCPh and of a carbene moiety, is formed; its structure has been determined by an X-ray study. In the case of aminopyridine, bidentate carbene complexes (the structure of which was confirmed by an X-ray study of (CO)4CrC (CH3)NHNC5H5) are formed, and these also react with PhCCPh to give for M = Mo, new pyrrolinones through alkyne/CO insertion followed by a 1,2 hydrogen shift. © 1991.

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