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Janice Smith, Joseph Hinton, and Karen Kugler
Sonochemistry in Organic Synthesis: Synthesis of Alkynyl Iodonium Salts
Presented at the First Annual, IU Northwest College of Arts and Sciences Research Conference, November 2004
Ultrasound has been used recently and effectively in many organic reactions, diminishing the
reaction times and increasing the yields. Sometimes reaction products that are not accessible by
conventional methods are obtained this way. Alkynyliodonium salts have emerged as valuable
reagents for organic synthesis in recent years. In this research project, preparations of alkynyl
iodonium salts using ultrasound are being studied. In particular, the effect of amplitude, time, and
method of synthesis using HMIB and HTIB with different alkynes will be discussed.
Maureen Petrunich, Janice Smith and Janushi Dalal
Sonochemistry in Organic Synthesis: Nucleophilic Substitution
Reactions of Alkynyl Iodonium Salts
Presented at the Second Annual, IU Northwest College of Arts and Sciences Research Conference, November, 2005
Ultrasound has been used recently and effectively in many organic reactions. The
use of this technique has diminished reaction times and has increased product
yields. Reaction products that are not accessible by conventional methods can be
obtained using sonochemistry. Alkynyl iodonium salts have emerged as valuable
reagents for organic synthesis in recent years. In this research project, the reaction
of these iodonium salts with different nucleophiles using ultrasound is examined.
In particular, reactions of the alkynyl iodonium salts using sonochemistry with
diethylmalonate, alkynide, and selenide ions will be discussed.
Gene Maya and Christopher Klonowski
Sonochemistry in Organic Synthesis: Nucleophilic Substitution Reactions of
Alkynyl Iodonium Salts
Presented at the Thirda Annual IU Northwest College of Arts and Sciences Research Conference, November 2006
Ultrasound has been used recently and effectively in various organic reactions. The use of this technique
has both diminished reaction times and increased product yields. Additionally, reaction products
that are not accessible by conventional methods can be obtained using sonochemistry. Alkynyl iodonium
salts have emerged as valuable reagents for organic synthesis in recent years. These alkynyl iodonium
salts can be formed by sonicating a terminal alkyne with [hydroxy(tosyloxy)iodo]benzene or
[hydroxy(mesyloxy)iodo]benzene. In particular, two of the alkynes used in this research to synthesize
the iodonium salts were 3,3-dimethyl-1-butyne and 1-heptyne. The reactions of the iodonium salts with
different ucleophiles were studied. The use of hypervalent iodine methodology along with sonication
resulted in a reactivity reversal of the terminal alkynes, which is very significant. Reactions of these
alkynyl iodonium salts using sonochemistry with diethylmalonate, alkynide, and selenide ions were
also investigated. Additionally, this research reports the impact of variables such as time and amplitude
of sonication on product yields.
Brandyn Mason, Christopher Klonowski and Gene Maya
SONOCHEMISTRY IN ORGANIC SYNTHESIS: NUCLEOPHILIC SUBSTITUTION REACTIONS OF ALKYNYL IODONIUM SALTS
Presented at the 13th Annual Indiana University Undergraduate Research Conference
Friday, November 30, 2007 at IU Southeast
Making Research Relevant
Ultrasound has been used recently and effectively in various organic reactions. The use of this technique has decreased reaction times and increased product yields. Additionally reaction products that are not accessible by conventional methods can be obtained by using sonochemistry. Alkynyl iodonium salts have emerged as valuable reagents for organic synthesis in recent years as well. The alkynyl iodonium salts are formed by sonicating a terminal alkyne, such as 3,3-dimethyl-1-butyne, 1-pentyne, and 1-heptyne, with [hydroxyl(tosyloxy)iodo]benzene or [hydroxyl(mesyloxy)iodo]benzene. The reactions of the iodonium salts with different nucleophiles such as diethylmalonate, alkynide, and selenide ions were studied. The use of hypervalent iodine methodology along with sonication resulted in reactivity reversal of the terminal alkynes, which is very significant. Additionally, this research reports the impact of variables such as time and amplitude of sonication on product yields.
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