Document Type and Release Option
Thesis (open access)
Dr. Karelle Aiken
The iodine-initiated hydration of internal alkynes is a novel, green, and inexpensive synthetic pathway in comparison with the commonly used transition metal catalyzed reactions. This can be a useful alternative in many fields, academic or industrial. This experimental design has been used successfully on terminal alkynes and is now being extended to internal alkynes. Through systematic probing of the reaction conditions, we have gleaned sufficient information to determine a strong mechanistic hypothesis based on neighboring group participation. Here in, we will report our result with a series of internal, keto alkynes reacted under ambient conditions with iodine in “wet” solvent. Preliminary data have revealed that acetonitrile is the best solvent for this reaction.
Shuber, Nicholas J. and Aiken, Karelle, "Iodine-Initiated Hydration of Internal Alkynes" (2017). Honors College Theses. 305.