Preparation and reactivity of persistent and stable silyl-substituted bisketenes

Autor:	Annette D. Allen, Da Chuan Zhao, Thomas T. Tidwell
Rok vydání:	1993
Předmět:	Diketone Silylation Trimethylsilyl Chemistry General Chemistry Biochemistry Medicinal chemistry Catalysis chemistry.chemical_compound Colloid and Surface Chemistry Reaction rate constant Molecule Reactivity (chemistry) Methanol Solvent effects
Zdroj:	Journal of the American Chemical Society. 115:10097-10103
ISSN:	1520-5126 0002-7863
DOI:	10.1021/ja00075a027
Popis:	2,3-Bis(trimethylsilyl)-1,3-butadiene-1,4-dione (1) is formed as the only product on thermolysis of 3,4-bis-(trimethylsilyl)cyclobut-3-ene-1,2-dione (2), and the rate of ring opening of 2 is comparable to that of substituted cyclobutenes and cyclobutenones. Photolysis of 2 also forms 1, which reacts with ethanol in a stepwise fashion with faster addition of one ethanol molecule to give an isolable monoketene 18, which reacts in a further slower step to give succinate diesters, accompanied by desilylation. 2,3-bis(tert-butyldimethylsilyl)-1,3-butadiene-1,4-dione (3), prepared analogously to 1, similarly adds one molecule of methanol to give the isolable monoketene 20, which then reacts to give dimethyl 2,3-Bis(tert-butyldimethylsilyl)succinate (21) as the major product
Databáze:	OpenAIRE
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