The nitrile oxides : versatile tools of theoretical and preparative chemistry / Ch. Grundmann, P. Grünanger
Grundmann, Christoph (författare)
Grünanger, Paolo (författare)
- ISBN 978-3-642-99993-2
- Berlin ; Springer-Vlg, 1971
- Engelska viii, 242 s.
Serie: Organische Chemie in Einzeldarstellungen, 0078-6225 ; 13
- Chapter I: Introduction -- A. Definition, Nomenclature -- B. History -- C. General Properties -- Chapter II: Physical Properties -- A. General -- B. Electronic Spectra -- Chapter III: Preparation -- A. General -- B. Formonitrile Oxide (Fulminic Acid) and Derivatives -- C. Other Nitrile Oxides -- 1. From Aldoximes -- 2. From Primary Nitroparaffins -- 3. From Fulminates -- D. Preparation in situ -- E. Functional Groups in Nitrile Oxides -- Chapter IV: Chemical Reactions Involving Only the Nitrile Oxide -- A. Isomerization to Isocyanates -- B. Deoxygenation to Nitriles -- C. Polymerization -- 1. Polymerization of Fulminic Acid -- 2. Polymerization of Other Nitrile Oxides -- Chapter V: Addition Reactions Leading to Cyclic Structures: 1,3-Dipolar Cycloadditions -- A. General -- B. Reactions with C=C Derivatives -- C. Reactions with C=C Derivatives -- D. Reactions with C=O and C=S Compounds -- E. Reactions with C=N Compounds -- F. Reactions with Nitriles -- G. Reactions with Other Unsaturated Systems -- Chapter VI: Addition Reactions Leading to Open-Chain Structures; 1,3-Additions -- A. General -- B. Addition of Hydrogen -- C. Addition of Water (Hydrolysis) -- D. Addition of Alcohols and Phenols -- E. Addition of Sulfides and Thiols -- F. Addition of Inorganic and Organic Acids and their Derivatives -- G. Addition of Ammonia and its Derivatives -- H. Addition of Azide, Cyanide and Thiocyanate Ions -- I. Addition of Metallo-Organic Compounds -- K. Addition of Free Radicals -- L. Other Addition Reactions -- Chapter VII: Miscellaneous Reactions -- Chapter VIII: Physiological Properties and Applications of Nitrile Oxides -- Chapter IX: Tabular Survey.
- From their discovery in the last decade of the nineteenth century on, the nitrile oxides comprised a rather small group of little-known and little-investigated unstable organic derivatives of hydroxylamine. Around 1950, the astonishingly wide variety of their reactions started to become gradually unveiled. This reactivity has made them increasingly important as valuable tools for many syntheses. Simultaneously, the newly discovered transformations raised interesting theoretical questions and their pursuit has generally enriched our understanding of reaction mechanisms of organic chemistry. At the same time, when nitrile oxides finally had won on their own a position of justified interest in the eyes of the organic chemist, came the discovery that fulminic acid, was in fact the parent member of this series. Thus, suddenly the nitrile oxides had acquired the most illustrious ancestry. Fulminic acid was discovered in 1800, at the dawn of modern chemistry, and since then the riddle of its true structure as well as the proteus-like variability of the molecule in its multitude of reactions has at one time or another attracted some of the most brilliant minds of organic chemistry, among them Berthollet, Gay-Lussac, Liebig, Wohler, Berzelius, Gerhardt, KekuTe, Griess, Armstrong, Holleman, Scholl, Nef, H. Wieland. The present authors readily confess that they too have succumbed to the fascination obviously emanating from the longest-known member as well as from the younger offspring of the nitrile oxide family. To their surprise, no review of this field has been attempted since Wieland's monograph of 1909, which covered mainly fulminic acid. One of the authors has recently published an article on the preparative aspects of nitrile oxides and a short review of their chemistry. The unexpectedly wide interest that these publications have found among chemists and members of related sciences has encouraged authors and publisher alike to present this monograph as the first comprehensive survey of this area.
- Nitrile oxides (LCSH)
- Organisk kemi
- 547.239.2 (UDK)
- 541.451 (UDK)
- 547/.44/4 (DDC)
- QD 262
- Ucebc (kssb/8 (machine generated))
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