Cis-Trans Isomeric Carotenoids, Vitamins A and Arylpolyenes

First Part: Isoprenic Polyenes. I. Carotenoids: Introduction Nomenclature Some Historical Remarks on the Stereoisomerism of Polyenes II. Number and Types of cis Carotenoids. Steric Hindrance III. Some Properties of cis Carotenoids 1. Relative Stabilities 2. Melting Points 3. Rotatory Power 4. Relative Adsorption Affinities IV. Cis-trans Isomerism and UV Spectra 1. Some Remarks on the Spectra of all-Trans Carotenoids 2. Spectral Effect of trans—> cis Isomerization in the Visible Region 3. Spectral Effect of trans—> cis Isomerization in the Near Ultraviolet Region: The cis-Peak 4. A Simple Theoretical Interpretation of Spectral Phenomena, Especially of the cis-Peak Effect 5. Spectra at Extremely Low Temperatures V. Preparation of cis Carotenoids by Direct Rearrangement of the All-trans Form 1. Thermal Methods of cis-trans Isomerization 2. Photochemical cis-trans Isomerization in the Absence of Catalysts 3. cis-trans Isomerization by Iodine Catalysis, in Light 4. cis-trans Isomerization by Acid Catalysis 5. cis-trans Isomerization by Contact with Active Surfaces 6. cis-trans Isomerization via Boron Trifluoride Complexes 7. Bio-Stereoisomerization VI. Preparation of cis Carotenoids by Total Synthesis VII. Naturally Occurring cis and Folycis Carotenoids 1. Mono- and Dicis Carotenoids 2. Polycis Carotenoids VIII. Some General Remarks on Configurational Assignments 1. Stereoisomeric Types 2. Number and Location of cis Double Bonds 3. Configuration and Infrared Spectrum IX. Configurational Assignments in Certain Stereoisomeric Sets 1. Stereoisomeric Sets with Two Hydroaromatic Terminal Groups 2. Stereoisomeric Sets with One Hydroaromatic and One Aliphatic Terminal Group 3. Stereoisomeric Sets with Two Aliphatic Terminal Groups 4. Stereoisomeric Sets with Two Aromatic Terminal Groups X. Lower-Molecular Weight Carotenoid-carboxylic Acids: Bixin and Crocetin Bixin Set Crocetin Set XI. Cis-trans Isomerism and Provitamin A Effect of Carotenoids XII. Vitamins A and Retinenes 1. Structural Relationships 2. Number and Character of cis Vitamins A and cis Retinenes 3. Cis-trans Isomerism and Spectra 4. Preparation of cis Vitamins A and cis Retinenes by Direct Rearrangement 5. Preparation of cis Isomers by Total Synthesis 6. Naturally Occurring cis Vitamins A and Retinenes 7. Chromatographic Separation of Stereoisomers 8. Some Methods used in Configurational Assignments 9. Systemic Bioeffects of cis-trans Isomeric Vitamins A and Retinenes 10. Some Stereochemical Aspects of Visual ProcessesSecond Part: Unbranched Arylpolyenes. Introductory Remarks XIII. I-Monoaryl-Polyenes I-Phenylbutadiene Set I-Phenylundecapentaenal-(II) Set XIV. α,ω-Diplienylpolyenes and Related Compounds 1. General Remarks 2. Stilbene Set 3. Diphenylbutadiene Set 4. Diphenylhexatriene Set 5. Diphenyloctatetraene Set 6. Sets Containing Bulky End Groups and a Short Conjugated System XV. Cumulenes with Aromatic Terminal Groups Bis-[2-Nitrodiphenylene]-Butatriene Set 1,4-Bis-[m-Nitrophenyl]-1,4-Diphenyl-Butatriene Set XVI. Polyene Azines Cinnamalazine Set Phenylpentadienalazine Set XVII. BibliographyIndex of AuthorsIndex of Subjects