Chemistry: Faculty Publications (1990-2023)
Hydration of 5-Oxo-1-Alkynes by a One-Pot Oxy-Iodination/Reduction Sequence: Synthesis of Methyl Ketones with Anchimeric Assistance
Document Type
Article
Publication Date
2012
Publication Title
Current Organic Synthesis
DOI
10.2174/15701794113106660069
ISSN
1875-6271
Abstract
Methyl ketone derivatives can be accessed from5-oxo-1-alkynesin 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.
Recommended Citation
Trossarello, Julia, Adegboyego Egunjobi, Whitney J. Morgan, Rayaj Ahamed, Karelle Aiken.
2012.
"Hydration of 5-Oxo-1-Alkynes by a One-Pot Oxy-Iodination/Reduction Sequence: Synthesis of Methyl Ketones with Anchimeric Assistance."
Current Organic Synthesis, 11 (3): 466-470: Bentham Science Publishers.
doi: 10.2174/15701794113106660069 source: http://www.eurekaselect.com/115167/article
https://digitalcommons.georgiasouthern.edu/chem-facpubs/2
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