Methyl ketone derivatives can be accessed from 5-oxo-1-alkynes in an iodine-initiated hydration of the terminal alkynes. Use
of molecular iodine in this manner is novel, inexpensive and a greener alternative to the traditional use of transition metal catalysts.
Herein, we report the results of a methodology study which sheds light on the underlying mechanism of this new, metal-free reaction.
Our findings indicate that the hydration of the alkyne proceeds via an important anchimeric assistance in which the neighboring keto
group participates with a 5-exo-dig cyclization.
Keywords: Anchimeric assistance, deiodination, hydration, ketone, metal-free, molecular iodine, terminal alkyne.
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Published on: 23 June, 2014
Page: [466 - 470]