Germylene reactions with quinones shed light on germylene phenone equilibria

Ryan D. Sweeder; Robyn L. Gdula; Bonnie J. Ludwig; Mark M. Banaszak Holl; Jeff W. Kampf

doi:10.1021/om0302589

Germylene reactions with quinones shed light on germylene phenone equilibria

Ryan D. Sweeder, Robyn L. Gdula, Bonnie J. Ludwig, Mark M. Banaszak Holl, Jeff W. Kampf

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

14 Citations (Scopus)

Abstract

Ge[CH(SiMe₃)₂]₂ (1) and Ge[N(SiMe ₃)₂]₂ (2) react with anthraquinone and naphthoquinone in a 2:1 ratio to form five-membered rings with the carbonyl oxygens and the ortho carbons of the adjacent aromatic ring. The reaction with 1,4-diacetylbenzene proceeds in a similar fashion with 1; however no reaction is observed with 2. Compounds 1 and 2 react with 1,2diacetylbenzene to yield a novel bicyclo species. In a previous report describing equilibria between 1 and phenones, it appeared that 2 did not undergo reaction to generate the five-membered ring with the accompanying formation of a conjugated triene. However, these quinone results indicate that an equilibrium can exist between 2 and a phenone moiety. In the reaction with quinones, a second equivalent of germylene effectively traps the conjugated triene by undergoing a 1,4-addition reaction. Unlike the initial triene formation, this second insertion is irreversible.

Original language	English
Pages (from-to)	3222-3229
Number of pages	8
Journal	Organometallics
Volume	22
Issue number	16
DOIs	https://doi.org/10.1021/om0302589
Publication status	Published - 4 Aug 2003
Externally published	Yes

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title = "Germylene reactions with quinones shed light on germylene phenone equilibria",

abstract = "Ge[CH(SiMe3)2]2 (1) and Ge[N(SiMe 3)2]2 (2) react with anthraquinone and naphthoquinone in a 2:1 ratio to form five-membered rings with the carbonyl oxygens and the ortho carbons of the adjacent aromatic ring. The reaction with 1,4-diacetylbenzene proceeds in a similar fashion with 1; however no reaction is observed with 2. Compounds 1 and 2 react with 1,2diacetylbenzene to yield a novel bicyclo species. In a previous report describing equilibria between 1 and phenones, it appeared that 2 did not undergo reaction to generate the five-membered ring with the accompanying formation of a conjugated triene. However, these quinone results indicate that an equilibrium can exist between 2 and a phenone moiety. In the reaction with quinones, a second equivalent of germylene effectively traps the conjugated triene by undergoing a 1,4-addition reaction. Unlike the initial triene formation, this second insertion is irreversible.",

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T1 - Germylene reactions with quinones shed light on germylene phenone equilibria

AU - Sweeder, Ryan D.

AU - Gdula, Robyn L.

AU - Ludwig, Bonnie J.

AU - Banaszak Holl, Mark M.

AU - Kampf, Jeff W.

PY - 2003/8/4

Y1 - 2003/8/4

N2 - Ge[CH(SiMe3)2]2 (1) and Ge[N(SiMe 3)2]2 (2) react with anthraquinone and naphthoquinone in a 2:1 ratio to form five-membered rings with the carbonyl oxygens and the ortho carbons of the adjacent aromatic ring. The reaction with 1,4-diacetylbenzene proceeds in a similar fashion with 1; however no reaction is observed with 2. Compounds 1 and 2 react with 1,2diacetylbenzene to yield a novel bicyclo species. In a previous report describing equilibria between 1 and phenones, it appeared that 2 did not undergo reaction to generate the five-membered ring with the accompanying formation of a conjugated triene. However, these quinone results indicate that an equilibrium can exist between 2 and a phenone moiety. In the reaction with quinones, a second equivalent of germylene effectively traps the conjugated triene by undergoing a 1,4-addition reaction. Unlike the initial triene formation, this second insertion is irreversible.

AB - Ge[CH(SiMe3)2]2 (1) and Ge[N(SiMe 3)2]2 (2) react with anthraquinone and naphthoquinone in a 2:1 ratio to form five-membered rings with the carbonyl oxygens and the ortho carbons of the adjacent aromatic ring. The reaction with 1,4-diacetylbenzene proceeds in a similar fashion with 1; however no reaction is observed with 2. Compounds 1 and 2 react with 1,2diacetylbenzene to yield a novel bicyclo species. In a previous report describing equilibria between 1 and phenones, it appeared that 2 did not undergo reaction to generate the five-membered ring with the accompanying formation of a conjugated triene. However, these quinone results indicate that an equilibrium can exist between 2 and a phenone moiety. In the reaction with quinones, a second equivalent of germylene effectively traps the conjugated triene by undergoing a 1,4-addition reaction. Unlike the initial triene formation, this second insertion is irreversible.

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JO - Organometallics

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ER -

Germylene reactions with quinones shed light on germylene phenone equilibria

Abstract

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