Benzoyl group, migration

To ascertain whether the benzoyl group migrates conceitedly or as a separate detached entity, House815 conducted the isomerization "f beozalaoetopbenono oxide in the presence of on equivalent amount i... 

Tenney, L.P., Boykin, D.W. Jr, and Lutz, R.E. (1966) Novel photocydization of a highly phenylated p.y-uri saturated ketone to a cyclopropyl ketone, involving benzoyl group migration. Journal of the American Chemical Society, 88 (8), 1835-1836. 

Chaudhary, A. G. Chordia, M. D. Kingston, D. G. I. A novel benzoyl group migration synthesis and biological evaluation of l-benzoyl-2-des(benzoyloxy)paclitaxel. J. Org. Chem., 1995, 60 3260-3262. 

TBDPSCl, NH4NO3, DMF, 72-96% yield. This reagent can be used to avoid benzoyl group migration that can occur under more basic conditions."... 

Tenney, L. R, Boykin, D. W., Lutz, R. E., Novel Photocyclization of a Highly Phenylated P.y Unsaturated Ketone to a Cyclopropyl Ketone Involving Benzoyl Group Migration, 7. Am. Chem. Soc. 1966, 88, 1835 1836. 

When the isoxazole (105.1) is treated with an excess of diazomethane at laboratory temperature, a [1, S]sigmatropic shift occurs and the benzoyl group migrates from the bridgehead position to an adjacent carbon (that derived from diazomethane)—a move which resembles the Van Alphen-Hauttel rearrangement [B-4]. 

An attractive route, which employs the Sharpless oxidation method, dihydoxylates methyl cinnamate with high enantioselectivity. After regio-selective esterification with trimethyl orthobenzoate, the amino-function is introduced via the azide). The desired product is obtained from benzoyl group migration. 

The reagent has been used widely in carbohydrate - chemistry. The method was found to be useful in cases where O-benzoyl group migration had been observed under basic conditions (eq 2), and has also been applied to inositol derivatives, when the same problem was encountered. 

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