118512-61-1

Basic information

• Product Name: O-triethylgermyl catechol
• Synonyms: O-triethylgermyl catechol
• CAS NO: 118512-61-1
• Molecular Weight: 381.095
• Mol File: 118512-61-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: O-triethylgermyl catechol(CAS DataBase Reference)
• NIST Chemistry Reference: O-triethylgermyl catechol(118512-61-1)
• EPA Substance Registry System: O-triethylgermyl catechol(118512-61-1)

Safety Data

• Hazardous Substances Data: 118512-61-1(Hazardous Substances Data)

Upstream product

• 3383-21-9 3,5-di-tert-butyl-o-benzoquinone 
• 37095-98-0 N,N-diphenyl-N-triethylgermylamine 
• 775-69-9 N-phenyl-N-triethylgermylamine 
• 59020-36-9 Bis--phenyl-amin 
• 23079-99-4 bis(triethylgermyl)methylamine 
• 1020-31-1 3,5-Di-tert-butylcatechol 
• 866-37-5 triethylgermyl dimethylamine 
• 1188-14-3 Triethylgerman 

Downstream Products

• 78100-52-4 2,2-diethyl(6,8-di-tert-butyl)-4,5-benzo-2-germa-1,3-dioxolane 
• 51639-37-3 C₆H₂(C(CH₃)3)2(OGe(C₂H₅)3)2 

Relevant articles and documents

Addition 1,4 de divers organo- et organohalogeno-hydrogermanes sur la di-t-butyl-3,5 orthoquinone

The thermal 1,4-addition of triorganohydrogermanes R3GeH(R=Et, Ph) with 3,5-di-t-butylorthoquinone leads to their corresponding mono-O-germylated catechols in good yields.Similarly, the organohalohydrogermanes give the 2,2-di-organo- (or 2,2-organohalo)(6,8-di-t-butyl)-4,5-benzo-2-germa-1,3-dioxolanes after dehydrochlorination of transient mono-O-chlorogermylated catechols.Since these reactions are only slightly dependent on solvent and radical initiators, the mechanism probably involves monoelectronic transfer with the formation of a radical anion pair in the first step.The ESR measurements show the transient formation of a paramagnetico-semiquinonic species which supports the proposed mechanism.

Reaction de derives a liaison germanium-azote (germylamines, cyclogermazanes et germa-imines transitoires) avec la di-t-butyl-3,5-orthoquinone

Several germanium-nitrogen compounds were treated with 3,5-di-t-butylorthoquinone (1).In the case of germylamines R3GeNMe2 (R = Et, Ph), 1,2 and 1,4 adducts were formed, as shown by 1H NMR spectroscopy.The thermally unstable 1,4 adduct, decomposes with nitrene elimination to give 2,2-dialkyl or 2,2-diaryl (6,8-di-t-butyl)-4,5-benzo-2-germa-1,3-dioxolane.The 1,2 adduct, through intermolecular redistribution, leads to digermyloxide (R3Ge)2O and a gem-diamine with partial regeneration of the starting quinone 1.These addition reactions proceed through a monoelectric transfer mechanism, with formation of a transient o-semiquinonic radical identified by ESR spectroscopy.This transient radical leads to O-germyl 3,5-di-t-butylcatechol by hydrogen abstraction from the solvent.The proposed mechanism explains the formation of the germylated compounds as well as the organic by-products.Similar reactions were observed between cyclodigermazanes and 1.The 1,4 cycloaddition generates germadioxolanes with nitrene expulsion, whereas the 1,2-cycloaddition leads to the germoxane and conjugated ketoimine, or diimine.The latter is a good trapping agent for the nitrene formed in the decomposition of the 1,4 adduct.Both the 1,4 and 1,2 cycloadduct decompositions imply transient germaimine formation.The same germaimine, formed at room temperature from intramolecular dehydrogenation of the hindered R2ClGeNHR' by 1,8-diazabicyclo-7-undecene) gives the same reaction products.