Lake Superior State University
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Alum Success

"I chose to transfer to Lake Superior State University because of the personal attention I would receive. I did not want to attend a large university where I would be a number lost in the masses. The well-rounded curriculum allowed me to obtain my position at John Deere. Having a good balance of theory and hands-on knowledge is critical for my position and Lake State gave me a good foundation in these skills."

Maria DiValentin, Mechanical Engineering 2001
Field Service Representative,
John Deere Power Systems
Waterloo, IA

School of Engineering

Senior Projects 2010-2011

Meet this year's project teams:

Team ISS logo
  Team ISS  

Innovative Solar Solutions
Concentrated Photovoltaic Module

Team RSS logo
  Team RSS  

Robotic Simulation Services
Virtual Commissioning of Automated Workcells

Team VIPERS logo
  Team VIPERS  

Vermilion Innovation Providers of Energy Research Solutions
Vermilion Point Project

Team Prototech logo
  Team PROTOTECH  

PROTOTECH
PDC Projects & LSSU Lab Refurbishment

Team SI logo
  Team S.I.  

Steering Innovations
Electronic Steering Column Clamping System

Team PRS logo
  Team PRS  

Pioneering Race Systems
Upgrade of SAE Mini Baja Transmission

Synthesis of Multicyclic Products ...

Josh Brown

“Synthesis of Multicyclic Products from Annulation Reaction of an Imadazoline and β-Hydroxy Carboxylic Acids”: Imidazolines are nitrogen containing hetercycles that can be found in natural products. They have unique properties particularly their ability to react with electrophiles and nucleophiles. If reacted with a molecule that contains both, imidazolines can undergo annulations to produce many interesting products. This study attempted to prepare a multicyclic product from the reaction of 1-benzyl-2-phenyl-2-imidazoline with salicyloyl chloride or salicylic acid under three different conditions to determine which was optimal. The first reaction is a two step process that uses salicyloyl chloride produced from salicylic acid. The salicyloyl chloride is then used in an annulations reaction with the imidazoline. Production of salicyloyl chloride by known methods failed. Conditions two and three attempted a similar annulations using the coupleing reagents BOP-Cl and EDC with salicylic acid and the imidazoline. These reagents work to bond the carboxylic acid to the imidazoline N and make the reaction one step. The EDC reaction failed to produce the right product, the BOP-Cl reaction appeared successful based on GCMS. However, during the purification the product was not able to be isolated.

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