454693-40-4

Upstream product

• 454693-42-6 cyclohexylidene-(6-iodo-benzo[1,3]dioxol-5-ylmethyl)-amine 
• 98799-35-0 2-iodo-4,5-(methylenedioxy)benzylamine 
• 108-94-1 cyclohexanone 
• 454693-46-0 N-(cyclohex-1-enyl)-N-[(2-iodo-4,5-methylenedioxy)benzyl]-2-chloroacetamide 

Relevant academic research and scientific papers

Is an iodine atom almighty as a leaving group for Bu3SnH-mediated radical cyclization? The effect of a halogen atom on the 5-endo-trig radical cyclization of N-vinyl-α-halo amides

The effect of a halogen atom as a leaving group on Bu3SnH-mediated 5-endo-trig radical cyclization of N-(cyclohex-1-enyl) α-halo amides was examined. The cyclization of α-chloro amides occurred with a high degree of efficiency, whereas the corresponding α-iodo congeners gave only limited quantities of cyclization products. A detailed study revealed that these phenomena could be attributed to the initial conformations of α-halo amides. The cyclizing ability of α-iodo amides can be restored with Bu3SnCl or Bu3SnF as an additive. The cyclization of an α-iodo amide in the presence of Bu3SnF could be applied to a short-step synthesis of lycoranes featuring sequential 5-endo-trig and 6-endo-trig radical cyclizations.