1 option
The Wolff-Kishner reduction and related reactions : discovery and development / David E. Lewis.
- Format:
- Book
- Author/Creator:
- Lewis, David E., author.
- Language:
- English
- Subjects (All):
- Wolff-Kishner reduction.
- Chemical reactions.
- Physical Description:
- xiii, 227 pages : illustrations ; 25 cm
- Place of Publication:
- Amsterdam, Netherlands : Elsevier, [2019]
- Contents:
- 1 The discoverers of the reaction p. 1
- Nikolai Matveevich Kizhner: A truly eventful life p. 1
- Kizhner's graduate research at Moscow p. 6
- Professor at Tomsk p. 9
- The Kizhner cyclopropane synthesis p. 13
- Kizhner, campus politics and the revolution of 1905 p. 15
- Kizhner in Soviet Moscow p. 27
- Ludwig Wolff p. 31
- The Wolff rearrangement p. 34
- 2 Discovery and priority p. 43
- 1911-1913: Kizhner's initial disclosures of the reaction p. 43
- 1911: Wolff's version of the reaction p. 50
- Settling the question of priority p. 52
- 3 Early studies of the reaction p. 57
- Mechanistic investigations p. 57
- The ionic mechanism p. 57
- Free radical intermediates in the Wolff-Kishner reduction? p. 60
- Free radical intermediates? ...maybe not... p. 61
- Free radical intermediates? ...then again, maybe yes p. 62
- Pyrazolines and N-alkylhydrazones p. 64
- Side reactions in the Wolff-Kishner reduction p. 65
- Early exploration of the scope and limitations of the reaction p. 68
- Higher terpenoids and steroids p. 70
- Heterocyclic compounds and alkaloids p. 78
- Haloazines: Reactions of halogenated pyridines, quinolines and purines with hydrazine p. 78
- Alkaloids p. 80
- Other alicyclic compounds p. 82
- Polycyclic aromatic hydrocarbons and their derivatives p. 83
- 4 The Huang-MinIon modification p. 91
- The Huang-MinIon modification of the Wolff-Kishner reduction p. 92
- The discoverer of the reaction p. 95
- Steroids and santonins p. 96
- Representative applications of the Huang-MinIon method p. 100
- Effects of steric hindrance p. 102
- Aromatic aldehydes and ketones p. 102
- Bile acids, steroids and triterpenes p. 105
- Other alicyclic systems p. 110
- Heteroaromatic aldehydes and ketones p. 112
- Alkaloids and cyclic amines p. 117
- Limitations of the Wolff-Kishner reduction p. 121
- A final word... p. 122
- 5 Modern adaptations of the Wolff-Kishner reduction p. 133
- Effects of steric hindrance on the Wolff-Kishner reaction p. 134
- Barton and Nagata modifications of the Wolff-Kishner reduction: "Forced" Wolff-Kishner reductions p. 137
- The Barton modification p. 137
- The Nagata modification p. 140
- The Henbest modification p. 143
- The Cram modification p. 146
- What about not using a base at all? Deoxygenation by reduction of sulfonylhydrazones p. 148
- The Caglioti modification p. 149
- The Hutchins modification p. 151
- The Myers modification p. 156
- Tosylhydrazones and strong bases: Alkenes and carbenes from carbonyl compounds p. 156
- Metal Alkyls: the Shapiro reaction p. 159
- Metal alkoxides: The Bamford-Stevens reaction p. 160
- 6 Kishner reduction-elimination of α-substituted ketones p. 169
- Reduction of α-amino-, α-alkoxy- and α-hydroxyketones p. 169
- Reduction of α-halo- and α-tosyloxyketones p. 176
- Systems resistant to the Kishner reduction-elimination p. 178
- The reaction of epoxyketones and 2-acylaziridines with hydrazine: The Wharton and aza-Wharton reactions p. 179
- Kishner reduction-elimination reactions of epoxyketones p. 179
- Acid-catalyzed reduction of epoxyketones by hydrazine: The Wharton reaction p. 181
- The reduction of 2-acylaziridines to allylamines by hydrazine: The aza-Wharton reaction p. 183
- The reaction of epoxyketones with tosylhydrazine: The Eschenmoser fragmentation p. 185
- 7 Deoxygenation in modern synthesis p. 191
- The Huang-Minion modification p. 191
- Natural products p. 191
- Cyclophanes p. 192
- Compounds for medicine p. 193
- Compounds for materials science and technology p. 199
- End-stage reactions in multistep syntheses p. 202
- The Barton modification p. 205
- The Nagata modification p. 206
- The Wharton and Aza-Wharton reactions p. 207
- The Eschenmoser fragmentation p. 208
- The Shapiro reaction p. 211
- Where to now? What modifications have we not tried yet? p. 214.
- Notes:
- Includes bibliographical references and index.
- Other Format:
- Ebook version :
- ISBN:
- 0128157275
- 9780128157275
- OCLC:
- 1048943544
The Penn Libraries is committed to describing library materials using current, accurate, and responsible language. If you discover outdated or inaccurate language, please fill out this feedback form to report it and suggest alternative language.