Potassium hydride in paraffin: A useful base for organic synthesis

Journal of Organic Chemistry

Volumn 71, Issue 23, 2006, Pages 8973-8974

  Taber, Douglass F ^a   Nelson, Christopher G ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CONDENSATION; PARAFFINS; SYNTHESIS (CHEMICAL); THERMAL EFFECTS;

PHOSPHONIUM SALT; UNSATURATED ALDEHYDES; WITTIG CONDENSATION;

POTASSIUM COMPOUNDS;

ALDEHYDE; ALIPHATIC COMPOUND; AROMATIC COMPOUND; BASE; ORGANIC COMPOUND; PARAFFIN; PHOSPHONIUM DERIVATIVE; POTASSIUM DERIVATIVE; POTASSIUM HYDRIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; HOMOGENATE; MOLECULAR STABILITY; ORGANIC CHEMISTRY; SOLID STATE; SYNTHESIS; TEMPERATURE DEPENDENCE; WITTIG REACTION;

ALDEHYDES; ALKENES; MOLECULAR STRUCTURE; PARAFFIN; POTASSIUM; STEREOISOMERISM;

EID: 33750874090     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061420v     Document Type: Article

References (22)

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2. (b) Brown, C. A.; Yamashita, A. J. Am. Chem. Soc. 1975, 97, 891.
3. For an early review of organic synthesis applications of KH, see Pinnick, H. W. Org. Prep. Proced. Int. 1983, 15, 199.
4. As of this writing, more than 4000 pages of this journal have been published in 2006. The use of KH has been reported just 12 times: (a) Kumaraswamy, G.; Padmaja, M.; Markondaiah, B.; Jena, N.; Sridhar, B.; Kiran, M. U. J. Org. Chem. 2006, 71, 337.
5. (b) Naya, S.; Ohtoshi, H.; Nitta, M. J. Org. Chem. 2006, 71, 176-184.
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16. The coating of air-sensitive catalysts with paraffin is a common industrial practice with many references in the patent literature. For examples, see (a) Fang, Y.; Liu, Y.; Ke, Y.; Guo, C.; Zhu, N.; Mi, X.; Ma, Z.; Hu, Y. Appl. Catal. A 2002, 235, 33.
17. (b) Kosak, K. M.; Kosak, M. K. U.S. Patent 5 413 924, 1995.
18. We have used this approach to stabilize sensitive catalysts: (c) Taber, D. F.; Frankowski, K. J. J. Org. Chem. 2003, 68, 6047.
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21. KH(P) prepared by the method outlined here is commercially available from Wilmington PharmaTech.
22. 13C multiplicities were determined with the aid of a JVERT pulse sequence, differentiating the signals for methyl and methine carbons as "d" and for methylene and quaternary carbons as "u".