1998
DOI: 10.1246/cl.1998.811
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Synthesis and Reactions of the First Stable 1-Germaallene

Abstract: The first stable 1-germaallene was synthesized by treatment of an extremely hindered alkylidenetelluragermirane with a large excess amount of hexamethylphosphorous triamide or by reductive dechlorination of the corresponding overcrowded (1-chlorovinyl)chlorogermane with t-butyllithium in THF. The germaallene was isolated as a colorless solid by the latter synthetic method and found to be fairly stable even in solution at room temperature, although it underwent an intramolecular cyclization at 80 °C in benzene.

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Cited by 59 publications
(50 citation statements)
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“…Thus, for the synthesis of the stibaallene ArSb@C@CR 2 , it appeared better to create the Sb@C double bond in the final step by a dechlorofluorination of a 2-chloro-3-fluorostibapropene with tert-butyllithium. Such a route was successfully used for the preparation of a heteroallene with a heavy group 14 element, the germaallene Tbt(Tip)Ge@C@CR 2 [12] (Tbt = 2,4,6-tris[bis(trimeth-ylsilyl)methyl]phenyl).…”
Section: Resultsmentioning
confidence: 99%
“…Thus, for the synthesis of the stibaallene ArSb@C@CR 2 , it appeared better to create the Sb@C double bond in the final step by a dechlorofluorination of a 2-chloro-3-fluorostibapropene with tert-butyllithium. Such a route was successfully used for the preparation of a heteroallene with a heavy group 14 element, the germaallene Tbt(Tip)Ge@C@CR 2 [12] (Tbt = 2,4,6-tris[bis(trimeth-ylsilyl)methyl]phenyl).…”
Section: Resultsmentioning
confidence: 99%
“…[17,18] Owing to this unique structuralf eature,s elones have been utilized as synthons in organic synthesis for an enduring period of time, and their use as ligating struts in complexation with transition metals has recently startedt od evelop. [19][20][21][22][23][24] Similart ot ellurones, monomeric selones also exhibit at endency to dimerize unless placed in as terically hindered alkyl environment or stabilized by electronic delocalization. [13,25] Imidazole selones, as pecial class of heteroketones, have gained increasing interest in recenty ears as efficient ligating agents in lieu of traditional N-heterocyclic carbenes.…”
Section: Introductionmentioning
confidence: 99%
“…[17,18] Owing to this unique structuralf eature,s elones have been utilized as synthons in organic synthesis for an enduring period of time, and their use as ligating struts in complexation with transition metals has recently startedt od evelop. [19][20][21][22][23][24] Similart ot ellurones, monomeric selones also exhibit at endency to dimerize unless placed in as terically hindered alkyl environment or stabilized by electronic delocalization. [13,25] Imidazole selones, as pecial class of heteroketones, have gained increasing interest in recenty ears as efficient ligating agents in lieu of traditional N-heterocyclic carbenes.…”
Section: Introductionmentioning
confidence: 99%