52203-12-0

Upstream product

• 65805-36-9 3-(2-iodoethoxy)prop-1-ene 

Downstream Products

• 40296-20-6 1-methyl-3-(prop-2'-en-1'-yl)pyrrolidin-2-one 
• 1001315-61-2 (Z)-7-(4-methyloxybenzyloxy)-4-(2'-(4-methyloxybenzyloxy)-ethyl)-hepta-1,4-diene 
• 88381-98-0 N-(1-phenyl-3-butenyl)benzylamine 
• 173914-18-6 (1S,4S,6S)-4-Hydroxy-6-(naphthalen-1-ylmethoxy)-cyclohex-2-ene-1,1-dicarboxylic acid allyl ester methyl ester 
• 173914-19-7 (1S,4S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-cyclohex-2-ene-1,1-dicarboxylic acid allyl ester methyl ester 
• 105526-85-0 (S)-5-(trityloxymethyl)pyrrolidin-2-one 
• 116983-75-6 allyl (3S)-3-dimethyl(phenyl)silylbutanoate 
• 31574-56-8 2,4-dinitro-benzenesulfenic acid allyl ester 
• 121190-17-8 2-propenyl N-phenylpropanimidate 

Relevant academic research and scientific papers

Lithium-Iodine Exchange Mediated Atom Transfer Cyclization: Catalytic Cycloisomerization of 6-Iodo-1-hexenes

Treatment of 6-iodo-1-hexene (1) in a variety of solvent systems with either MeLi or PhLi at room temperature or above effects clean cycloisomerization of 1 to (iodomethyl)cyclopentane (4). This novel transformation, which is mediated by rapid and reversible lithium-iodine exchange processes, most likely involves the following discrete steps: (i) generation of 5-hexenyllithium (2) from 1 by exchange with MeLi or PhLi, (ii) irreversible cyclization of 2 to give (cyclopentylmethyl)lithium (3) and (iii) virtually complete conversion of 3 to (iodomethyl)cyclopentane (4) via a highly favorable lithium-iodine exchange equilibrium. The isomerization sequence 1 → 4 has been found to be effectively catalytic in PhLi when conducted in hydrocarbon-ether solvent mixtures at room temperature.