106435-59-0

Basic information

• Product Name: α-triisopropylsilyl-α-diazoacetone
• Synonyms: α-triisopropylsilyl-α-diazoacetone
• CAS NO: 106435-59-0
• Molecular Weight: 240.421
• Mol File: 106435-59-0.mol

Chemical Properties

• CAS DataBase Reference: α-triisopropylsilyl-α-diazoacetone(CAS DataBase Reference)
• NIST Chemistry Reference: α-triisopropylsilyl-α-diazoacetone(106435-59-0)
• EPA Substance Registry System: α-triisopropylsilyl-α-diazoacetone(106435-59-0)

Safety Data

• Hazardous Substances Data: 106435-59-0(Hazardous Substances Data)

Upstream product

• 2684-62-0 diazoacetone 
• 80522-42-5 triisopropylsilyl trifluoromethanesulfonate 

Downstream Products

• 39910-61-7 3-diazo-4-hydroxy-4-phenyl-butan-2-one 
• 5381-93-1 1-hydroxy-1-phenyl-3-butanone 
• 1411736-85-0 1-diazo-4-hydroxy-4-(4-methoxyphenyl)butan-2-one 
• 1411736-95-2 4-cyclohexyl-1-diazo-4-hydroxybutan-2-one 

Relevant articles and documents

Advances in the TBAF-induced aldol-type addition of α-trialkylsilyl-α-diazoacetones: TIPS versus TES

α-Triisopropylsilyl-α-diazoacetone (TIPS-diazoacetone) underwent high-yielding “diazo-side” Mukaiyama aldol-type addition with a range of aryl and alkyl aldehydes when subjected to stoichiometric amount of tetrabutylammonium fluoride at ?16 °C, in Et2O. Robustness of the TIPS group makes TIPS-diazoacetone a stable surrogate for α-triethylsilyl-α-diazoacetone, on which generation of the corresponding carbanion can still be efficiently achieved under nucleophilic, weakly basic and practical conditions. These results highlight the synthetic potential that can be expected from TIPS-diazoacetone, promising building block for the convergent elaboration of highly functionalised versatile diazocarbonyl compounds.

TIPS-Diazoacetone Aldol Addition: Mechanistic Aspects and Contribution to the Synthesis

Aldol addition of α-triisopropylsilyl-α-diazoacetone (TIPS-diazoacetone), promoted by excess lithium diisopropylamide (LDA), was developed and applied to the synthesis of original C-TIPS diazoaldols, C-TIPS diazoketols, and a related Mannich-type product. An unprecedented mechanistic pathway has been proposed, involving a lithiated triazene intermediate resulting from the nucleophilic addition of LDA on the diazo moiety, supported by experimental results and DFT calculations.

Thermal Decomposition of α-Diazo-α-(trialkylsilyl)alkanones - Intramolecular C/H Insertion of Siloxyalkylidenecarbene Intermediates

α-Diazo-α-(trialkylsilyl)alkanones 6 have been prepared by silylation of primary α-diazo ketones 4 with trialkylsilyl triflates 5.Diazo compounds 6 are decomposed in boiling benzene to give 1-oxa-2-sila-4-cyclopentenes 7 and 9.Evidence is presented that this transformation proceeds via alkylidenecarbenes 17 which undergo 1,5-cyclization by carbene insertion into a SiC-H bond.