Dear researchers, i kindly ask you to help me with the following aspect: in scheme 4 (of j.org. chem, vol.66,No.23, 2001) it is shown that nucleophile attacks on the acyliminium intermediate and iodine attacks the enecarbamate. What does this difference bring about?
Dear Swathi,
You did NOT mention the authors' names and the paper pages. It more appropriate if you can attach the paper itself.
Rafik
Synthesis of 2,3-Disubstituted Pyrrolidines and Piperidines via One-Pot Oxidative Decarboxylation−β-Iodination of Amino Acids
Ernest Suarez has posted the full text of this journal in researchgate
Hi, both iodine and water are nucleophiles but water attacks only acyliminium intermediates while iodine does not, why is to so, kindly let me know the reason for difference in reactivity of these two intermediates
Dear Swathi,
The reaction mechanism is depicted in Scheme 4: Iodine (I2) functuins af an electrophile where I+ attack the double bond, the double bond is opened and gives a cationic species which is then being attacked by a nucleophile.
Therefore, the function of I2 is an electrophile whereas, water or OH- is a nucleophile.
Hoping this will be helpful,
Rafik
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