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Synthesis of Switchable Diazobenzene Nano-compounds, Fries type rearrangement of Carbonates and Ethers, Synthesis of Dicyano Stillbenes, Aromatics Bromination, Synthesis of Benzothiazoles and Thiophenes

Zargarani, Dordaneh | 2009

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  1. Type of Document: Ph.D. Dissertation
  2. Language: Farsi
  3. Document No: 39164 (03)
  4. University: Sharif University of Technology
  5. Department: Chemistry
  6. Advisor(s): Matloubi Moghaddam, Firouz
  7. Abstract:
  8. In this project, Fries rearrangement of aryl benzyl ethers and ary benzyl carbonates, using catalyst and microwave irradiation in solvent-less system have been studied, and Benzylated phenols which have attracted a great deal of interest, due to their medicinal properties, were synthesized. The solvent-free Fries reactions have many advantages such as: reduced pollution, low costs, and simplicity in process and handling. We report the use of N-benzyl DABCO tribromide as an electrophilic bromine source and one of the OATBs for one-step oxidative coupling procedure of benzyl cyanides into Symmetrical α,ά -dicyanostilbenes. The reaction proceeds easily with higher yields and shorter reaction time when electron withdrawing group functioned on aromatic ring. Also this reagent is used for the selective deprotection of dithioacetals. Continuation of our study bromination of phenols and substituted anilines have been studied. N-benzyl DABCO tribromide used as a bromination reagent for regioselective bromination of phenols and substituted anilines at room temprature. The thio-Claisen rearrangement has been an excellent method for the formation of C-C bonds and is used for the construction of highly substituted thiophenes. We report an ultimately simple and efficient one-step synthesis of 2-arylbenzothiazoles by the reaction of thiobenzanilides in the presence of N-Bromosuccinimide. In photo-switchable nano-compounds, we have synthesized Thiol-ended and Isocyanide-ended diazobenzenes, after fixing them on the gold surface, the properties of Trans and Cis isomers as photo-witchable surface modifiers before and after Ultra Violet irradiation have been studied
  9. Keywords:
  10. Fries Rearrangement ; Benzothiazole ; Thiophene ; Dicyanostillbene ; Photo-Swichable Nanocompounds

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