117788-01-9

Upstream product

• 13361-64-3 trimethyl(propargyl)silane 
• 117787-96-9 Ethyl N-benzyl-N-carbamate 
• 117787-97-0 tert-Butyl N-benzyl-N-carbamate 
• 117787-98-1 Benzyl N-benzyl-N-carbamate 
• 622-72-0 N-(4-methoxylbenzylidene)benzylamine 

Downstream Products

• 142055-13-8 5-Acetyl-3-benzyl-4-(4-methoxyphenyl)-6-methyl-3,4-dihydro-2H-1,3-oxazin-2-one 
• 117806-53-8 rel-(4R,5S)-5-Acetyl-3-benzyl-4-(4-methoxyphenyl)-6-methylenetetrahydro-1,3-oxazin-2-one 
• 142055-08-1 3-Benzyl-4-(4-methoxyphenyl)-6-methylenetetrahydro-1,3-oxazin-2-one 
• 142055-10-5 3-Benzyl-4-(4-methoxyphenyl)-6-methyl-3,4-dihydro-2H-1,3-oxazin-2-one 
• 142055-11-6 rel-(4R,5R)-3-Benzyl-5-bromo-4-(4-methoxyphenyl)-6-methylenetetrahydro-1,3-oxazin-2-one 

Relevant academic research and scientific papers

Intermolecular reactions of N-alkoxycarbonyliminium ions with propargyltrimethylsilane; oxazinone versus allene formation

Intermolecular reactions of N-alkoxycarbonyliminium ions with propargyltrimethylsilane mainly lead to 6-(trimethylsilyl)methyl-3,4-dihydro-2H-1,3-oxazinones, formed by intramolecular trapping of a stabilized β-sily vinylic cation. α-Allenyl carbamates are obtained as minor products. The oxazinone/allene ratio is dependent on the nature of the Lewis acid and the solvent used.

OXAZINONE VERSUS ALLENE FORMATION IN THE REACTION OF N-ALKOXYCARBONYLIMINIUM IONS WITH PROPARGYLTRIMETHYLSILANE

Reaction of N-alkoxycarbonyliminium ions with propargyltrimethylsilane, promoted by Lewis acid, yield in most cases mixtures of allenes G and oxazinones H.