8.12 Reduction of C X to CH 2

作者: J.W. Burton

DOI: 10.1016/B978-0-08-097742-3.00814-4

关键词: ChemistryAldehydeMethyl groupClemmensen reductionIonic bondingKetoneDeoxygenationOrganic chemistryHydrogenolysisMethylene

摘要: The complete reduction of the carbonyl group an aldehyde or ketone to a methylene/methyl is generally achieved using well-known Wolff–Kishner and Clemmensen reductions these two transformations form majority chapter. A range useful procedures along with possible side reactions presented; examples will be mainly taken from recent literature. use ionic hydrogenation metal-catalyzed hydrogenolysis, predominantly aromatic ketones aldehydes, also presented. Other methods are briefly discussed.

参考文章(210)
Robert O. Hutchins, Marygail K. Hutchins, Reduction of CX to CH2 by Wolff–Kishner and Other Hydrazone Methods Comprehensive Organic Synthesis. ,vol. 1, pp. 327- 362 ,(1991) , 10.1016/B978-0-08-052349-1.00230-4
이관희, 홍종인, 이우영, None, Orthocyclophanes. 6. Hexamethoxy Derivatives of [$1_6$]Oethocyclophane Bulletin of The Korean Chemical Society. ,vol. 17, pp. 661- 663 ,(1996)
W.E. Barnett, L.L. Needham, R.W. Powell, Tritylone ethers: Cleavage, stability and selectivity of formation☆ Tetrahedron. ,vol. 28, pp. 419- 424 ,(1972) , 10.1016/0040-4020(72)84004-3
László Kürti, Barbara Czakó, K. C. Nicolaou, E. J. Corey, Strategic Applications of Named Reactions in Organic Synthesis: Background and Detailed Mechanisms ,(2005)
J.-P. Yong, J.-W. Wang, H. A. Aisa, L.-J. Liu, Synthesis of glycyrrhetic acid derivatives Chemistry of Natural Compounds. ,vol. 44, pp. 194- 196 ,(2008) , 10.1007/S10600-008-9012-4
Carlos Cativiela, María D. Díaz-de-Villegas, Ana I. Jiménez, A straightforward synthesis of (−)-(1S,2R)-Allonorcoronamic acid using D-mannitol as the chiral source Tetrahedron-asymmetry. ,vol. 6, pp. 2067- 2072 ,(1995) , 10.1016/0957-4166(95)00269-U
Tetsuaki Tanaka, Kimiya Maeda, Hidenori Mikamiyama, Yousuke Funakoshi, Kenji Uenaka, Chuzo Iwata, Synthetic studies on aromadendrane-type compounds. III. Stereoselective total syntheses of (+)-aromadendrene and (−)-alloaromadendrene Tetrahedron. ,vol. 52, pp. 4257- 4268 ,(1996) , 10.1016/0040-4020(96)00086-5
W. B. Motherwell, C. J. Nutley, The role of zinc carbenoids in organic synthesis Contemporary Organic Synthesis. ,vol. 1, pp. 219- 241 ,(1994) , 10.1039/CO9940100219