230285-14-0

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 1206146-95-3 5-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-pentan-1-ol 
• 87184-80-3 5-tert-butyldimethylsilyloxypentanal 
• 83067-20-3 5-(tert-butyldimethyl-silyloxy)pentan-1-ol 
• 111-29-5 1 ,5-pentanediol 
• 230285-12-8 5-(tert-butyldiphenylsiloxy)-1-phenyl-1-pentanol 
• 230285-11-7 5-(tert-butyldiphenylsiloxy)-1-phenyl-1-pentanone 
• 1011-62-7 5-hydroxy-1-phenylpentan-1-one 

Downstream Products

• 230285-15-1 1-phenyl-5-(N-phthalimidoxy)-1-(2-tetrahydropyranyloxy)pentane 
• 15212-27-8 2-benzyltetrahydrofuran 
• 230285-16-2 1-phenyl-5-(N-phthalimidoxy)-1-pentanol 
• 230285-17-3 1-(acetoxy)-1-phenyl-5-(N-phthalimidoxy)pentane 
• 230285-18-4 1-(diethylphosphatoxy)-1-phenyl-5-(N-phthalimidoxy)pentane 
• 230285-19-5 1-(diphenylphosphatoxy)-1-phenyl-5-(N-phthalimidoxy)pentane 
• 145475-10-1 5-phenyl-1,4-pentanediol 
• 1011-61-6 1-phenylpentane-1,5-diol 

Relevant academic research and scientific papers

Vicinal bisheterocyclizations of alkynes via nucleophilic interception of a catalytic platinum carbene

A novel platinum-catalyzed double heterocyclization of propargylic ethers is described. The transformation exploits the intermediacy of a key α,β-unsaturated carbene. The reactivity of this carbene is such that systems can be developed which avoid a complicating 1,2-hydrogen migration, allowing remarkable versatility in the selective syntheses of oxygen- and nitrogen-containing vicinal bis-heterocyclic compounds.

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.