21464-01-7

Upstream product

• 93-55-0 1-phenyl-propan-1-one 
• 230285-29-7 1-(acetoxy)-2-methyl-1-phenyl-5-(N-phthalimidoxy)pentane 
• 230285-28-6 2-methyl-1-phenyl-5-(N-phthalimidoxy)-1-pentanol 
• 67173-95-9 methyl-4 oxo-5 phenyl-5 pentanoate de methyle 
• 230285-23-1 2-methyl-1-phenyl-1,5-pentanediol 
• 230285-24-2 5-(tert-butyldiphenylsiloxy)-2-methyl-1-phenyl-1-pentanol 
• 230285-26-4 2-methyl-1-phenyl-1-(2-tetrahydropyranyloxy)-5-pentanol 
• 230285-31-1 2-methyl-1-phenyl-1-(diphenylphosphatoxy)-5-(N-phthalimidoxy)pentane 
• 230285-30-0 2-methyl-1-phenyl-1-(diethylphosphatoxy)-5-(N-phthalimidoxy)pentane 

Relevant academic research and scientific papers

Inter- and intramolecular pathways for the formation of tetrahydrofurans from β-(phosphatoxy)alkyl radicals. Evidence for a dissociative mechanism

β-(Phosphatoxy)alkyl radicals generated by photolysis of Barton PTOC esters in the presence of allyl alcohol and tert-butyl mercaptan undergo nucleophilic substitution followed by 5-exo-trig radical ring closure leading to tetrahydrofurans in good yield and with high trans selectivity. β- (Phosphatoxy)alkyl radicals obtained by intramolecular hydrogen 1,5- abstraction with an alkoxyl radical undergo nucleophilic displacement providing tetrahydrofurans. The ensemble of results, including the effects of leaving groups and substituents, strongly support a dissociative mechanism for these radical nucleophilic displacement reactions.

Synthesis of tetrahydrofurans by a tandem hydrogen atom abstraction/ radical nucleophilic displacement sequence

(equation presented) The reaction of a series of 5-(N-phthalimidoxy)-1-phenyl-1-(diphenylphosphatoxy)pentanes with triphenyltin hydride and AIBN provides alkoxy radicals which undergo 1,5-hydrogen atom abstraction to give β-(phosphatoxy)alkyl radicals. These radicals then take part in a radical nucleophilic displacement leading, after chain transfer, to tetrahydrofurans.