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TITLE
CERTIFICATE
DECLARATION
ACKNOWLEDGEMENT
CONTENTS
1. INTRODUCTION
1.1 Introduction
1.2 Chloromethyleneimiuium Salts: Reactions with Carbonyl Compounds.
1.3 Heterocumulenes: Reactions with Carbonyl Compounds
1.4 β-Alkylthioethylenic Aldehydes: Applications in the Synthesis of Substituted Phenols
1.5 Reactions of Chloromethyleneiminium Salts with Carbonyl Compounds
1.6 Reactions of β-Oxodithioesters with Heterocumulenes.
1.7 References
2. CHLOROMETYLENEIMINIUM SALTS AND HETEROCUMULENES: APPLICATIONS IN ORGANIC SYNTHESIS
2.1 Introduction
2.2 Chloromethyleneiminium Salts: Reactions with Carbonyl Compounds
2.2.1 Mechanistic Considerations
2.2.2 Reactions of Acyclic Ketones
2.2.3 Reactions of Cyclic Ketones
2.2.4 Reactions of α, β-Unsaturated Acyclic Ketones.
2.2.5 Reactions of α, β-Unsaturated Cyclic Ketones
2.2.6 Reactions of Acyclic 1, 3-Diketones
2.2.7 Reactions of Cyclic 1, 3-Diketones
2.3 Reactions of Heterocumulenes
2.3.1 Reactions with Nucleophiles
2.3.2 Cycloaddition Reactions
2.4 References
3. β-ALKYLTHIOETHYLENIC ALDEHYDES: SYNTHESIS AND APPLICATIONS IN THE PREPARATION OF SUBSTITUTED PHENOLS
3.1 Introduction
3.1.1 Synthesis of Aromatic Compounds from Acyclic Precursors
3.1.1.1 Synthesis of Substituted Phenols
3.1.1.2 Synthesis of Other Substituted Aromatic Compouds
3.1.1.3 Annulation Reactions on Heterocyclic Precursors
3.2 Results and discussion
3.2.1 Synthesis of β-Alkylthioethylenic Aldehydes
3.2.2 Cyclotrimerisation Reactions of Dithioketals
3.2.3 The Reactions of 3-Butylthio-2-methylpent-2-enal 58b with Ketones
3.2.4 Reaction with Substituted Benzyl Methyl Ketones.
3.2.5 Reactions of β-Alkylthioethylenic Aldehyde 58b and Dibenzyl Ketone
3.2.6 Reactions of 3-Aryl-3-butylthiopropenaldehydes 58 f-k with Dibenzyl Ketones
3.2.7 Reaction of β-Butylthio-3-naphthylpropenaldehyde 581 with Dibenzyl Ketone
3.3 Conclusions
3.4 Experimental
3.4.1 General Procedure for the Synthesis of Dithioketals from Carbonyl Compounds
3.4.2 General Procedure for the Preparation of β-Alkylthioethylenic Aldehyde.
3.4.3 Reaction of (E) -3-Butylthio-2-methylpent-2-enal with Diethyl Ketone: Formation of 3-Ethyl 2, 4, 6-trimethyl phenol 104
3.4.4 Reaction of (E) -3-Butylthio-2-methylpent-2-enal with Substituted Benzyl Methyl Ketone: General Procedure
3.4.5 Reaction of 3-Butylthio-2-methylpent-2-enal with Dibenzyl ketone: Formationof 3-Ethyl-4-methyl 2.6-diphenyl phenol 121
3.4.6 Reaction of β-Alkylthioethylenic Aldehydes with Dibenzyl ketone: General Procedure
3.4.7 Reaction of 3-Butylthio 3-naphthyl prop-2-enal with Dibenzylketone: Formation of 2, 6-Diphenyl-3- (2-naphthyl) phenol 125
3.5 References
4. REACTIONS OF CARBONYL COMPOUNDS WITH CHLOROMETHYLENEIMINIUM SALTS
4.1 Introduction
4.1.1 General Methods for the Synthesis of Pyran-4-one Derivatives
4.2 Results and Discussion
4.2.1 Reactions of 1-Aryl-2-propanones with Chloromethyleneiminium Salt
4.2.2 Reaction of Dibenzyl Ketone with Chloromethyleneiminium Salt
4.2.3 Reaction of 2, 2-Bis (butylthio) -l, 3-Diphenylpropane withChloromethyleneiminium Salt
4.2.4 Reaction of Phenoxyacetone with Chloromethyleneiminium Salt
4.2.5 The Reaction of Benzyl acetone with Chloromethyleneiminium Salt
4.2.6 Reactions of Acyl Ketenedithioacetals with Chloromethyleneiminium Salt
4.3 Conclusions
4.4 Experimental
4.4.1 Reactions of Substituted Phenyl Acetones with Vilsmeier Reagent: Formation of 3-Formyl-4-pyrones
4.4.2 Reaction of m-Anisyl Acetone with the Vilsmeier Reagent: Formation of 2-Chloro-5-methoxynaphthalene-1, 3-dicarboxaldehyde 85
4.4.3 Reaction of 1-phenyl butan-2-one with the Vilsmeier reagent: Formation of 3-Methyl-5-phenylpyran-4-one 87
4.4.4 Reaction of Dibenzyl Ketone with Vilsmeier Reagent: Formation of 3, 5-Bis (N, N-diethylamino) - 2, 4-diphenylpent-2, 4-dienal 89
4.4.5 Reaction of Phenoxy Acetone with Vilsmeier Reagent: Formation of 3-Chloro-5-N, N-dimethylamino-2 formyl-4-phenoxy 2, 4-pentadienal 95.
4.4.6 Reaction of Benzyl Acetone with Vilsmeier Reagent: Formation of 4-Hydroxy 6- (2-phenylethy1) -5-phenylmethyl benzene 1, 3-dicarboxaldehyde 102
4.4.7 Reaction of Dibenzyl Ketone Dithioketal with Vilsmeier Reagent: Formation of 3, 5-Diphenyl-4-pyrone 6
4.4.8 Reaction of 4-Bismethylthio-3-phenyl-3-butene-2-one with Vilsmeier Reagent: Formation of 3-Chloro-4-aryl-5-methylthio-2, 4-pentadienethioicacid S-methyl ester 113
4.5 References
5. REACTIONS OF β-OXODITHIOESTERS WITH HETEROCUMULENES
5.1 Introduction
5.1.1 β-Oxodithioesters and Dithiocarboxylic acids: General Methods for Synthesis
5.1.2 β-Oxodithioesters and Dithiocarboxylic Acids: Reactions
5.1.2.1 Sythesis of 2H-Thiopyran-2-thiones
5.1.2.2 Formation of Other Heterocycles
5.1.3 General Methods for the Synthesis of 1, 3-Thiazetidines
5.2 Results and Discussion
5.2.1 Reactions of β-Oxodithioesters with DCC
5.3 Conclusions
5.4 Experimental
5.4.1 Reaction of β-Oxodithioesters with 1, 3-Dicyclohexylcarbodiimide: Formation of 1, 3-Thiazetidines 49 General procedure
5.5 References