Formation of germenes from bis(germavinylidene)

Wing Por Leung; Kwok Wai Kan; Cheuk Wai So; Thomas C.W. Mak

doi:10.1021/om7002706

Formation of germenes from bis(germavinylidene)

Wing Por Leung^*, Kwok Wai Kan, Cheuk Wai So, Thomas C.W. Mak

^*Corresponding author for this work

Chinese University of Hong Kong

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

20 Citations (Scopus)

Abstract

A series of germenes have been synthesized from the bis(germavinylidene) [(Me₃SiN=PPh₂)₂C= Ge→Ge=C(PPh ₂=NSiMe₃)₂] (1). The reaction of 1 with 2,2,6,6-tetramethylpiperidine N-oxide afforded [(Me₃SiN=PPh ₂)₂C=Ge(ONCMe₂C₃H ₆CMe₂)₂] (2). Germavinylidene, the dissociation derivative of 1, underwent [1+4] cycloaddition with azobenzene, followed by a 1,3-H shift to give [(Me₃SiN=PPh₂)₂C= Ge(o-C₆H₄NHNPh)] (3). Treatment of 1 with benzil afforded the [1 + 4] cycloaddition compound [(Me₃-SiN=PPh₂) ₂C=Ge{O(Ph)C=C(Ph)O}] (4). The results showed that the germavinylidene moiety dissociated from 1 acts as a synthon for the preparation of various germenes by addition to the germanium-(II) center. The molecular structures of 2-4 have been determined.

Original language	English
Pages (from-to)	3802-3806
Number of pages	5
Journal	Organometallics
Volume	26
Issue number	15
DOIs	https://doi.org/10.1021/om7002706
Publication status	Published - Jul 16 2007
Externally published	Yes

ASJC Scopus Subject Areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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title = "Formation of germenes from bis(germavinylidene)",

abstract = "A series of germenes have been synthesized from the bis(germavinylidene) [(Me3SiN=PPh2)2C= Ge→Ge=C(PPh 2=NSiMe3)2] (1). The reaction of 1 with 2,2,6,6-tetramethylpiperidine N-oxide afforded [(Me3SiN=PPh 2)2C=Ge(ONCMe2C3H 6CMe2)2] (2). Germavinylidene, the dissociation derivative of 1, underwent [1+4] cycloaddition with azobenzene, followed by a 1,3-H shift to give [(Me3SiN=PPh2)2C= Ge(o-C6H4NHNPh)] (3). Treatment of 1 with benzil afforded the [1 + 4] cycloaddition compound [(Me3-SiN=PPh2) 2C=Ge{O(Ph)C=C(Ph)O}] (4). The results showed that the germavinylidene moiety dissociated from 1 acts as a synthon for the preparation of various germenes by addition to the germanium-(II) center. The molecular structures of 2-4 have been determined.",

author = "Leung, {Wing Por} and Kan, {Kwok Wai} and So, {Cheuk Wai} and Mak, {Thomas C.W.}",

year = "2007",

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AU - Leung, Wing Por

AU - Kan, Kwok Wai

AU - So, Cheuk Wai

AU - Mak, Thomas C.W.

PY - 2007/7/16

Y1 - 2007/7/16

N2 - A series of germenes have been synthesized from the bis(germavinylidene) [(Me3SiN=PPh2)2C= Ge→Ge=C(PPh 2=NSiMe3)2] (1). The reaction of 1 with 2,2,6,6-tetramethylpiperidine N-oxide afforded [(Me3SiN=PPh 2)2C=Ge(ONCMe2C3H 6CMe2)2] (2). Germavinylidene, the dissociation derivative of 1, underwent [1+4] cycloaddition with azobenzene, followed by a 1,3-H shift to give [(Me3SiN=PPh2)2C= Ge(o-C6H4NHNPh)] (3). Treatment of 1 with benzil afforded the [1 + 4] cycloaddition compound [(Me3-SiN=PPh2) 2C=Ge{O(Ph)C=C(Ph)O}] (4). The results showed that the germavinylidene moiety dissociated from 1 acts as a synthon for the preparation of various germenes by addition to the germanium-(II) center. The molecular structures of 2-4 have been determined.

AB - A series of germenes have been synthesized from the bis(germavinylidene) [(Me3SiN=PPh2)2C= Ge→Ge=C(PPh 2=NSiMe3)2] (1). The reaction of 1 with 2,2,6,6-tetramethylpiperidine N-oxide afforded [(Me3SiN=PPh 2)2C=Ge(ONCMe2C3H 6CMe2)2] (2). Germavinylidene, the dissociation derivative of 1, underwent [1+4] cycloaddition with azobenzene, followed by a 1,3-H shift to give [(Me3SiN=PPh2)2C= Ge(o-C6H4NHNPh)] (3). Treatment of 1 with benzil afforded the [1 + 4] cycloaddition compound [(Me3-SiN=PPh2) 2C=Ge{O(Ph)C=C(Ph)O}] (4). The results showed that the germavinylidene moiety dissociated from 1 acts as a synthon for the preparation of various germenes by addition to the germanium-(II) center. The molecular structures of 2-4 have been determined.

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Formation of germenes from bis(germavinylidene)

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