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TITLE
DEDICATION
CERTIFICATE
DECLARATION
CONTENTS
PREFACE
ACKNOWLEDGEMENT
LIST OF ABBREVIATIONS AND SYMBOLS
1. REDUCTION OF THE ORGANIC COMPOUNDS USING LITHIUM ALUMINUM HYDRIDE: A REVIEW
1.1. Introduction
1.2. Functional groups reduced using LAH
Table 1.1 List of functional groups reduced by LAH
1.3. Reduction of aldehydes and their derivatives
1.4. Reduction of ketones and their derivatives
1.5. Reduction of carboxylic acids and their derivatives
1.5.1. Acids
1.5.2. Acid chlorides
1.5.3. Acid anhydrides and lactones
1.5.4. Esters
1.5.5. Amides, Imides and Lactones
1.5.6. Nitriles
1.6. Reduction of nitro, nitroso, azo and azido groups
1.6.1. Nitro compounds
1.6.2. Nitroso, azo and azido compounds
1.7. Reduction of halogen substituted compounds
1.7.1.Reduction of halogeno compounds in presence of catalysts
1.8. Reduction of alcohols and phenols
1.9. Reduction of epoxides
1.10. Reduction of hydrocarbons and heterocycles
1.10.1. Hydrocarbons
1.10.2. Heterocycles
1.11. Reduction of sulphur compounds
1.12. Solvents used in the reduction using LAH
Table 1.2 Solubility of LAH in various solvents
1.13. Mechanism of the reduction using LAH
Molecular orbital picture of the nucleophilic addition to the carbonyl group
1.14. Decomposition of LAH-substrate complex
2. THE REDUCTION OF CARBONYL / CARBOXYL / ESTER DIFUNCTIONALIZED COMPOUNDS
2.1. Introduction
2.2. Results and discussion
Table 2.1 List of the compounds reduced by LAH
2.2.1. The reduction of dicarboxylic acids
1. The reduction of phthalic acid (2.30)
2. The reduction of N- (2-carboxyphenyl) aminoethanoic acid (2.31)
3. The reduction of (2-carboxy) phenoxyethanoic acid (2.32)
2.2.2. The attempt for the reduction of potassium hydrogen phthalate
2.2.3. The reduction of various alkyl / aryl hydrogen phthalates
2.2.4. The reduction of methyl hydrogen isophthalate
2.2.5. The reduction of methyl hydrogen terephthalate
2.2.6. The reduction of alkyl N- (2-carboxyphenyl) aminoethanoate
2.2.7. The reduction of (2-formyl) phenoxyethanoic acid
2.2.8. The reduction of N- (2-carboxyphenyl) aminomethyl phenyl ketone
2.2.9. The reduction of (2-acetoxy/benzoyloxy) phenyl methyl ketone
2.2.10. The reduction of methyl (2-benzoyloxy/phenyIacetoxy) benzoate
2.3. Experimental
2.3.1. General
2.3.2 Preparation of starting materials
1. Preparation of N- (2-carboxyphenyl) aminoethanoic acid
2. Preparation of (2-carboxy) phenoxyethanoic acid (2.32)
3. Preparation of methyl/benzyl/isopropyl/hydrogn phthalate
4. Preparation of benzhydryl/1-phenylethy 1hydrogen phthalate
5. Preparation of t-butyl hydrogen phthalate (2.34f)
6. Preparation of methyl hydrogen isophthalate/terephthalate
7. Preparation of methyl/elhyl N- (2-carboxyphenyl) amino ethanoate
8. Preparation of (2-formyl) phenoxyethanoic acid (2.38)
9. Preparation of N- (2-carboxyphenyl) aminomelhyl phenyl ketone (2.39)
10. Preparation of (2-acetoxy) phenyl methyl ketone (2.40a)
11. Preparation of (2-benzoyloxy) phenyl methyl ketone (2.40b)
12. Preparation of methyl (2-benzoyloxy) benzoate (2.41a)
13. Preparation of 2-methyl (2-phenylacetoxy) benzoate (2.41b)
2.3.3 Reduction of the compounds using LAH
3. THE REDUCTION OP THE NITRO-CARBONYL / CARBOXYL / ESTER / AMIDE DIFUNCTIONALIZED COMPOUNDS
3.1. Introduction
Table 3.1List of nitro-carbonyl/carboxyl/ester/amide difunctionalizedcompounds reduced by LAI-I
3.2 Results and Discussion
3.2.1. The reduction of nitro and ester difunctionalized compounds
1. The reduction of nitrophenyl benzoate (3.7a-c) and nitrophenyl ethanoate
2. The reduction of ethyl 2-nitrophenoxyethanoate
3.2.2. The reduction of nitro and carbonyl difunctionalized compounds
1. The reduction of 2-nitrophenoxymethyl phenyl ketone
3.2.3. The reduction of nitro and carboxyl difunctionalized compounds
1. The reduction of 2-N- (2-nitrophenyImethyl) aminobenzoic acid
2. The reduction of nitrobenzoic acids
3.2.4. The reduction of nitro and amide difunctioanlized compounds
1. The reduction of nitrobenzanilides
2. The reduction of N- (nitrop11enyl) benzamides (3.14a-c)
3.3. Experimental
3.3.1. Preparation of the starting materials
1. Preparation of nitrophenyl benzoates (3.7a-c)
2. Preparation of nitrophenyl ethanoates (3.8a-c)
3. Preparation of ethyl 2-nitrophenoxyethanoate (3.9)
Preparation of phenacyl bromide
4. Preparation of 2-nitrophenoxymethyl phenyl kctonc (3.10)
5. Preparation of 2-N- (2-nitrophenylmethy1) anlinobenzoic add (3.11)
6. Preparation of nitrobenzanilides (3.13a-r)
7. Preparation of N- (nitrophenyl) benzamides (3.14il-c)
3.3.2 Reduction of nitro and ester difunclionalized compounds.
1. Reduction of nitrophenyl benzoates (3.7a-c)
2. Reduction of nitrophenyl ethanoates (3.8a-c)
3. Reduction of ethyl 2-nitrophenoxyethanoate (3.9)
4. Reduction of 2-nitrophenoxymethyl phenyl ketone (3.10)
5. Preparation of 1-phenylethanol
6. Reduction of 2-N- (2-mtrophenyImethy1) aminobenzoic acid (3.11)
6. Reduction of nitrobenzoic acids (3.121-c)
7. The reduction of nitrobenzanilides (3.13 a-c)
8. Reduction of N- (nitropheny1) benzamides (3.14 a-c)
4. THE REDUCTION OF DINITRO, NITRO-HALOGENO, HALOGENO-CARBOXYL / ESTER AND NITRO-OXIMINO DIFUNCTIONALIZED COMPOUNDS
4.1. The reduction of dinitro compounds
1. The reduction of 1, 3-dinitrobenzene (4.5)
2. The reduction of 2-nitrophenyl nitmphenoxymethanes (4.6a, b)
3. The redaction of 2, 2-dinitrodiphenyl ether (4.7)
4. The reduction of 2, 2-dinitrodiphenylamine (4.8)
5. The reduction of (bis-2-nitroanilino) methane (4.9)
4.2. The reduction of nitro-halogeno difunctionalized compounds
4.2. The reduction of the halogenonitrobenzcnes (4.27a-c, 4.28, 4.29)
1. The reduction of 2-bromomethylnitrobenzene (4.27a)
2. The reduction of 3-bromomethylnitrobenzene (4.27%)
3. The reduction of 4-bromomethylnitrobenzene (4.27~)
4. The reduction of 4-chloromethylnitrobenzene (4.28)
5. The reduction of 4-iodomethylnitrobenzene (4.29)
4.3. The reduction halogeno-carboxyl / ester difunctionalized compounds
1. The reduction of 2, 3-dibromo-3-phenyl propanoate (4.32a)
2. The reduction of 2, 3-dibromo-3-phenylpropanoic acid (4.32b)
4.4. The reduction of nitro-oximino difunctionalized compound:
1. The reduction of 2-nitrobenzaldoxime (4.42)
4.5. Experimental
4.5.1 The preparation of the starting materials
4.5.2 The redaction of dinitro compounds
4.5.3 The reduction of halogeno-nitro compounds
4.5.4 Reduction of halogeno-carboxyl /ester compounds
4.5.5 The reduction of the nitro-.oximino compound
5. SUMMARY
REFERENCES