945627-99-6

Basic information

• Product Name: (Z)-4-methyl-4-tert-butyl-3-[(dimethyl-p-dimethylaminophenylsilyl)methylene]-3-(p-tosyl)-1-azetidin-2-one
• Synonyms: (Z)-4-methyl-4-tert-butyl-3-[(dimethyl-p-dimethylaminophenylsilyl)methylene]-3-(p-tosyl)-1-azetidin-2-one
• CAS NO: 945627-99-6
• Molecular Weight: 484.735
• Mol File: 945627-99-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (Z)-4-methyl-4-tert-butyl-3-[(dimethyl-p-dimethylaminophenylsilyl)methylene]-3-(p-tosyl)-1-azetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-4-methyl-4-tert-butyl-3-[(dimethyl-p-dimethylaminophenylsilyl)methylene]-3-(p-tosyl)-1-azetidin-2-one(945627-99-6)
• EPA Substance Registry System: (Z)-4-methyl-4-tert-butyl-3-[(dimethyl-p-dimethylaminophenylsilyl)methylene]-3-(p-tosyl)-1-azetidin-2-one(945627-99-6)

Safety Data

• Hazardous Substances Data: 945627-99-6(Hazardous Substances Data)

Upstream product

• 167258-38-0 3-amino-3,4,4-trimethyl-1-pentyne 
• 98-59-9 p-toluenesulfonyl chloride 
• 875612-04-7 N-(1-tert-butyl-1-methyl-2-propynyl)-p-toluenesulfonamide 
• 201230-82-2 carbon monoxide 
• 2516-75-8 <4-(N,N-dimethylamino)phenyl>dimethylsilane 

Relevant articles and documents

Silylation-desilylation of propargyl amides: rapid synthesis of functionalised aldehydes and β-lactams

Propargyl functionalised β-silylalkenals were easily prepared starting from suitable propargyl compounds by a silylformylation process. In particular the use of propargyl tosyl amides allowed the synthesis of α,β-unsaturated aldehydes through a two-step sequence of silylformylation-desilylation reactions. TBAF was employed to induce the desilylation process that was performed under very mild experimental conditions and occurred along with an elimination step of the tosylamido moiety affording 2-methylaryl-2-alkenals with good yields and stereoselectivity. When the tosyl amides were reacted with a hydrosilane in the presence of catalytic amounts of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) α-silylmethylene-β-lactams were synthesised through a silylcarbocyclisation process. A high chemoselectivity towards the β-lactam was observed when dialkyl propargyl amides were employed. The obtained β-lactams were easily transformed into the corresponding methylaryl-β-lactams by fluoride induced aryl migration-desilylation with total retention of configuration of the migrating group and complete stereoselectivity towards the more stable β-lactam (E)-isomer.