DEVELOPMENT OF C-F BOND IN ORGANIC MOLECULES AND THEIR APPLICATIONS

Abstract

The present work has been carried out to design the methodology and synthesis of aliphatic and aromatic fluoroorganic compounds containing the C-F bond and overcome some of the limitations reported in the literature. Chapter 1 provides a general description of fluoro-organic chemistry, the effect of fluorination on organic compounds, and their applications in various fields. The literature discussed in this chapter covers various fluorination mechanisms, including direct fluorination, electrochemical fluorination, nucleophilic fluorination, electrophilic fluorination, and radical fluorination, used for the synthesis of fluoroorganic compounds. This chapter also covers the different reagents used for the generation of the C-F bond in aliphatic and aromatic organic molecules. Chapter 2 covers the materials and methods, which describe different materials and instruments used in experimentation. The section explains the procedures for the synthesis of fluoroacetophenone derivatives and the synthesis of 3,7-difluorinatedoxindole derivatives. The methods for the -fluorination of acetophenone derivatives in a Fe(NO3)3·9H2O/KBr/TBAF mediated reaction and synthesis of 3,7-difluorinated oxindole derivatives, from indoles via Selectfluor mediated fluorination have been given in this chapter. This chapter also mentions the procedure for the synthesis of 3-indoleacetic acids, used as raw material. The characterisation data of the synthesized fluorinated compounds, as well as the synthesized starting materials, with different spectroscopic techniques, the determined melting points, and physical states of the synthesized compounds are also mentioned in this chapter. The general Method for the evaluation of flame retardancy of the selected synthesized compounds as per UL 94 has also been covered in this chapter. Chapter 3 is the results and discussion, which covers a detailed explanation about the design of the methodology for fluorination, optimization of reaction conditions, and synthesis and characterization of different fluorinated molecules. It also covers the detailed procedure for the preparation of polyurethane films, their testing, and results. To synthesize the 3,7-difluorinated oxindole derivatives, the ester of indoleacetic acid was synthesized by reaction with various alcohols. Chapter 4 summarized the work done, discussed the prospects and societal impact of the work. This chapter is followed by the references used in the thesis.