Investigation of the Reaction of Dithiocarbamic Acid Salts with Carbonyl Compounds (Ketones and Aldehydes), Epoxides and Ortho Esters

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Hajiloo Shayegan, Mojtaba | 2013

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Type of Document: M.Sc. Thesis
Language: Farsi
Document No: 44095 (03)
University: Sharif University of Technology
Department: Chemistry
Advisor(s): Mahmoodi Hashemi, Mohammed; Ziyaei Halimehjani, Azim
Abstract:
In the first section, for the first time, a reaction of dithiocarbamic acid salts with carbonyl compounds has been investigated in the presence of BF3.OEt2. The reaction is temperature dependent meaning that the reaction gives two different products at low and high temperatures. At 15-20 0C, the 2-iminium-1,3-dithietane is the main product.As the reaction temperature goes up, formation of gem-bis(dithiocarbamates) is dominant.In addition, deprotection of gem-bis(dithiocarbamates) was investigated by using of nitric acid as the only deprotecting agent. The structure of a 2-iminium-1,3-dithietane was confirmed by X-ray crystallographic analysis.
In the second and third sections, in our aim for investigation of the reaction of other substrates with dithiocarbamic acid salts and synthesizing target molecules, two different compounds were examined. Epoxy styron was used to prepare 1,3-dithiolane ring and ortho esters were examined to afford 1,3-dithietane ring. All the reactions mentioned above lead to remarkably high yields of products
Keywords:
1,3-Dithietane ; Orthoesters ; Dithiocarbamate Salt ; Epoxide ; Carbonyl Compounds