Subscribe

Subscribe to our Newsletter and get informed about new publication regulary and special discounts for subscribers!

ILCPA > Volume 83 > A Facile Autoxidation of an Allylic Alcohol in Air
< Back to Volume

A Facile Autoxidation of an Allylic Alcohol in Air

Full Text PDF

Abstract:

An (4E,6E)-alkadienyl alcohol which is a solid compound which can be stored at rt, upon dissolving into a suitable solvent undergoes facile autoxidation (4E,6E)-alkadienyl alcohol 1 in air at room temperature. The result is complete decompose leading to a mixture of products, including benzaldehyde (24%) and cinnamaldehyde (29%). Possible mechanistic explanations for the autoxidation are discussed.

Info:

Periodical:
International Letters of Chemistry, Physics and Astronomy (Volume 83)
Pages:
41-47
Citation:
F. A. Mosa and A. Whiting, "A Facile Autoxidation of an Allylic Alcohol in Air", International Letters of Chemistry, Physics and Astronomy, Vol. 83, pp. 41-47, 2019
Online since:
August 2019
Export:
Distribution:
References:

[1] M. G. Simic, J. Chem. Educ. 1981, 58, 125-131.

[2] P. E. Correa, G. Hardy, D. P. Riley, J. Org. Chem. 1988, 53, 1695-1702.

[3] J. H. Lee, Photooxidation and photosensitized oxidation in linoleic acid, milk, and lard. PhD thesis, 2002, The Ohio State University, Columbus, OH, USA.

[4] E. N. Frankel, Prog. Lipid Res. 1980, 19, 1-22.

[5] a) G. N. Maw, C. Thirsk, J.-L. Toujas, M. Vaultier, A. Whiting, Synlett, 2004, 1183-1186; b) Batsanov, A. S.; Knowles, J. P.; Whiting, A. J. Org. Chem. 2007, 72, 2525-2532; c) A. S. Batsanov, J. P. Knowles, A. P. Lightfoot, G. Maw, C. E. Thirsk, S. J. R. Twiddle, A. Whiting, Org. Lett., 2007, 9, 5565-5568; d) J. P. Knowles, V. E. O'Connor, A. Whiting, Org. Biomol. Chem., 2011, 9, 1876-1886.

DOI: https://doi.org/10.1021/ol7025262

[6] a) A. R. Hunt, S. K. Stewart, A. Whiting, Tetrahedron Lett., 1993, 34, 3599-3602; b) S. K. Stewart, A. Whiting, J. Organomet. Chem., 1994, 482, 293-300; c) S. K. Stewart, A. Whiting, Tetrahedron Lett., 1995, 36, 3925-392.

DOI: https://doi.org/10.1016/s0040-4039(00)73646-x

[7] C. Morrill, R. H. Grubbs, J. Org. Chem. 2003, 68, 6031-6034.

[8] N. Jiang, A. J. Ragauskas, Tetrahedron Lett. 2006, 47, 197-200.

[9] T. W Greene, P. G. M Wuts, Protective Groups in Organic Synthesis, 3rd ed.; 1999, John Wiley & Sons: New York.

Show More Hide
Cited By:
This article has no citations.