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  • TITLE
  • CERTIFICATE
  • DECLARATION
  • ACKNOWLEDGEMENT
  • CONTENTS
  • 1. INTRODUCTION
  • 1.1. Ketene Dithioacetals
  • 1.2 Functionalized Ketene Dithioacetals
  • 1.3 Alkenoyl Ketene Dithioacetals
  • 1.4 AIdol type Condensation Reactions of Acyl Ketene Dithioacetals
  • 1.5 Reactions of Acyl Ketene Dithioacetals with Chloro-methylene Iminium Salts
  • 1.6 References
  • 2. FUNCTIONALIZED KETENE DITHIOACETALS IN ORGANIC SYNTHESIS
  • 2.1 Introduction
  • 2.2 Synthesis of Functionalized Ketene Dithioacetals
  • 2.3 Functionalized Ketene Dithioacetals in Organic Synthesis
  • 2.3.1 α-Oxo Ketene Dithioacetals
  • 2.3.2 Nitro Ketene Dithioacelals
  • 2.4 Conclusions
  • 2.5 References
  • 3. ALDOL TYPE CONDENSATION REACTIONS OF ACYL KETENE DITHIOACETALS
  • 3.1 Introduction
  • 3.2 Results and Discussion
  • 3.2.1 The reactions of 3- (bis (methylthio) melhylene]pentane-2, 4-dione with substituted benzaldehydes
  • Fig.1 HNMR Spectrum (250 MHz) of compound 7a
  • Fig.2
  • Fig.3 Mass Spectrum (EIMS) of compound 7a
  • Fig.4 1R Spectrum (KBr) of compound 7a
  • 3.2.2 The reactions of 3-bis (methylthio) methylene pentane-2, 4-dione with substituted benzaldehydes under acid catalyzed conditions
  • Fig.5 H NMR Spcctrum (200 MHz) of compound 27
  • Fig.6
  • Fig.7
  • Fig.8 Mass Spectrum (EIMS) of compound 27
  • Fig.10 H NhlR Spectrum (200 MHz) of compound 28
  • Fig.11 C NMR Spectrum (50.3 MHz) of compound 28
  • Fig.12 Mass Spectrum (EIMS) of compound 28
  • 3.2.3 The reaction of 3- (1, 3-dithiolan-2 ylidene) -2, 4-pentanedione with aromatic aldehydes
  • Fig.13 IR Spectrum (KBr) of compound 28
  • Fig.14 H NMR Spectrum (250 MHz) of compound 29a
  • Fig.15
  • Fig.16 Mass Spectrum (EIMS) of compound 29a
  • Fig.17 IR Spectrum (KBr) of compound 29a
  • Fig.18 H NMR Spectrum (90 MHz) of compound 31a
  • Fig.19 Mass Spectrum (EIMS) of compound 31a
  • Fig.20 IR Spectrum (KBr) of compound 31a
  • 3.2.4 Reaction of t- (1, 3-dithiolan-2 ylidene) -1-phenyl-l, 3-butanedione with aromatic aldehyde:
  • Fig.21 H NMR Spectrum (90 MHz) of compound 33a
  • 3.2.5. Reaction of 1, 7-bis (phenyl) -4- (1, 3-dithiolan-2ylidene) -I, 6-hepla-diene-3, 5-dione with sulfoxonium methylide
  • Fig.22 Mass Spectrum (EIMS) of compound 33a
  • Fig.23 IR Spectrum (KBr) of compound 33a
  • 3.2.6. Reaction of 1, 7-bis (phenyl) -4- (1, 3-dithiolan-2-ylidene) -1, 6-heptadiene-3, 5-dione with sulfoxonium methylide
  • Fig.24 H NMR Spectrum (200 MHz) of cornpoul~d3 7
  • Fig.25 I3c NMR Spectrum (50.3 MHz) of compound 37
  • Fig.26 Mass Spectrum (EIMS) of compound 37
  • Fig.27 IR Spectrum (KBr) of compound 37
  • 3.2.7 Cycloaddition reactions of bis (cinnamoyl) ketene dithioacetal
  • 3.3 Conclusions
  • Fig.28 H NMR Spectrum (300 MHz) of 40
  • Fig.29 C NMR Spectrum (22.3 MHz) of 40
  • Fig.30 FABMS of compound 40
  • 3.4 Experimental
  • 3.4.1 Preparation of 3-[bis (methylthio) methylene]pentane-2, 4-dine. (3)
  • 3.4.2 The reactions of 3-[bis (methylthio) methylene]pentane-2, 4-dionewith substituted benzaldehydes.
  • GENERAL PROCEDURE
  • 3.4.3 The reaction of 3-bis (methylthio) methylene pentane-2, 4-dione withsubstituted benzaldehydes under acid catalyzed condition.
  • GENERAL PROCEDURE
  • 3.4.4 Preparation of 3- (1, 3-dithiolan-2-ylidene-2, 4-pentanedioe) (5)
  • 3.4.5 The reaction of 3- (1, 3-dithiolan-2-ylidene) -2, 4-pentanedione witharomatic aldehydes.
  • GENERAL PROCEDURE
  • 3.4.6 Preparation of 2- (1, 3-dithiolan-2-ylidene) -1-phenyl-1, 3-butanedione (32)
  • 3.4.7 Reaction of 2- (1, 3-dithiolan-2-ylidene) -I-pheny~-1, 3-butanedionewith aromatic aldehydes
  • GENERAL PROCEDURE
  • 3.4.8 Reaction of 1, 7-bis (phenyl) -4- (1, 3-dithiolan-2-ylidene) -1, 6-heptadiene-3, 5-dione with sulfoxonium methylide
  • 3.4.9 Preparation of 1, 7-bis- (N, N-dimethylamino) -4- (1, 3-dithiolan-2-ylidene) -1, 6-heptadiene-3, s-dione
  • 3.4.10 Cycloaddition reactions of bis (cinnamoy1) ketene dithioacetal 29a
  • 3.5 References
  • 4. REACTIONS OF ACYL KETENE DITHIOACETALS WITH CHLOROMETHYLENIC IMINIUM SALTS
  • 4.1 lntroduction
  • 4.1.1 Reactions of functionalized ketene dithioacetals with chloromethyleneiminium salts
  • 4.1.2 Vilsmeier-Haack reactions of dithioketals
  • 4.2 Results and Discussion
  • 4.2.1 Reactions of acyl ketene dithioacetals with Vilsmeier reagent
  • Fig.1 H NMR Spectrum (90 MHz) of compound 21
  • Fig.2 Mass Spectum (EIMS) of compound 21
  • Fig.3 IR Spectum (KBr) of compound 21
  • 4.2.2 Reduction of acyl ketene dithioacetals followed by reaction withchloromethylene iminium salts
  • Fig.4 GCMS of compounds 44 & 45
  • Fig.5 H NMR Spectrum (90 MHz) of compound 47
  • Fig.6
  • Fig.7 IR Spectrum (KBr) of compo~~4l~7
  • Fig.8 H NMR Spectrum (90 MHz) of compound 53
  • Fig.9 Mass Spectrum (EIMS) of compound
  • Fig.10 IR Spectrum (KBr) of compound 53
  • 4.2.3 Addition of Grignard reagent to acyl ketene dithioacetals followedby reaction with chloromethylene iminium salts
  • 4.3 Conclusions
  • 4.4 Experimental
  • 4.4.1 Reaction of acyl ketene dithioacetals 20 and 36 with Vilsmeierreagent
  • GENERAL PROCEDURE
  • 4.4.2 Reaction of ketene dithioacetal 38 with Vilsmeier reagent
  • 4.4.3 Preparation of 4-[bis (methylthio) methylenel-2, s-heptadine1, 7-dial
  • 4.4.4 Reduction of 3- (1, 3-dithiolan-2-ylidene) -2, 4-pentanedione
  • 4.4.5 Preparation of 4- (1, 3-dithiolan-2-ylidene) -2, S-hexadiena and 4- (1, 3-dithiolan-2-ylidene) -2, 5-heptadiene-1, 7-dial
  • 4.4.6 Preparation of 4- (1, 3-dithiolan-2-ylidene) -2-pentcr1al
  • 4.4.7 Preparation of 2, 2-dimethylthio-4-phenyl-2H-pyran
  • 4.5 References