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Hydration of 5-Oxo-1-Alkynes by a One-Pot Oxy-Iodination/Reduction Sequence: Synthesis of Methyl Ketones with Anchimeric Assistance

[ Vol. 11 , Issue. 3 ]

Author(s):

Julia Trossarello, Adegboyega Egunjobi, Whitney J. Morgan, Rayaj Ahamed and Karelle S. Aiken   Pages 466 - 470 ( 5 )

Abstract:


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.

Affiliation:

Chemistry Department, PO Box 8064, Georgia Southern University, Statesboro, GA 30460, USA.

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