The Tour of Collective Wisdom presents:
May Require Mojo


Literature procedures do not always give consistent results. Sometimes this is the fault of the chemist, and sometimes the fault of the chemistry. This list contains reaction chemistry from the literature that is capricious or difficult to reproduce. This page is a pure reflection of visitor input - it has never been edited internally (disclaimer: the opinions displayed here are not those of the site administrator).

Procedure:
Reference:
Verification:
Procedure Reference This procedure requires mojo Number of responses Percent who agree
Reduction/halogenation of triple bonds TL, 1971, 1821 agree disagree 2 100%
Reduction/halogenation of triple bonds JACS, 2010, 132, 8219 agree disagree 2 100%
Magnesiation of pyridines with TMP-Mg-x A. Krasovskiy, V. Krasovskaya, P. Knochel, Angew. Chem. 2006, 118, 3024 %96 3027; Angew. Chem. Int. Ed. 2006, 45, 2958 %96 2961. agree disagree 3 100%
Organocatalysed direct arylation C. Sun, H. Li, D. Yu, M. Yu, X. Zhou, X. Lu, K. Huang, S. Zheng, B. Li, Z. Shi: Nature Chem. 2010, 2, 1044-1049 agree disagree 136 97%
Preparation of organo selenides Singh, D.; Alberto, E. E.; Rodrigues, O. E. D.; Braga, A. L. Green Chem. 2009, 11, 1521-1524. agree disagree 127 94%
Reduction of nitrile to aldehyde with 2.3 equiv. of DIBAL-H Chem. Eur. J., 2002, 8(9), 2000-2004 agree disagree 105 83%
DIBAl-H reduction of simple methyl esters to aldehydes J. Am. Chem. Soc.; 1990; 112(17) pp agree disagree 101 76%
Benzylic Oxidation with IBX JACS 124 (10), 2245-2258 (2002) agree disagree 122 69%
Roush's asymmetric crotylation J. Am. Chem. Soc.; 1990; 112(17) pp 6339 - 6348; http://dx.doi.org/10.1021/ja00173a023 agree disagree 53 66%
Iodination of alcohol with CeCl3·7H2O/NaI System J.Org.Chem. 2000, 65, 2830-2833 agree disagree 37 64%
DIBAl-H reduction of simple methyl esters to aldehydes Organic Syntheses agree disagree 444 59%
Novel system for decarboxylative bromination of a,b-unsaturated carboxylic acids with diacetoxyiodobenzene Chem. Pharm. Bull. 57(11), 1243-1245 (2009) agree disagree 14 57%
Shi Epoxidation JACS 1997, 119 (46), 11224-11235 agree disagree 36 47%
Schwartz's Reagent Organic Syntheses agree disagree 109 46%
Activation of allylbarium Organic Syntheses agree disagree 91 43%
[Pd(nbd)(Ma)] K.Itoh, Chem. Lett, 1977, 877-880 agree disagree 29 41%
Efficient Preparative Rentes to 6,6&%238242;-Dibromo-2-2&%238242;-bipyridine and 6-Bromo-2,2&%238242;-bipyridine 10.1080/00397919008052832 agree disagree 5 40%
Shapiro Reaction Org React. 1976, 23, 405 agree disagree 77 38%
Bellamy reduction JACS 89, 1994 agree disagree 29 37%
Dess Martin Periodinane J. Org. Chem. 1983, 48, 4155. or J.Org.Chem., 64 (1999) 4537. agree disagree 149 33%
Acetonide of tartaric acid Van Deusen et al. Org Syn, Ann. Vol. 68, p.92; Coll. Vol. 8, p.155 agree disagree 87 21%
Cross-metathesis of terminal olefins Grubbs agree disagree 224 20%
Evans Auxiliary Aldol Condensation Organic Syntheses agree disagree 431 6%
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