Mechanism of the oxidation of para-substituted 1-phenylethanols with sodium hypochlorite in acetic acid

Author:

Sakai Ayano,Hendrickson David G.,Hendrickson William H.

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference23 articles.

1. Mohrig, J. R.; Nienhuls, D. M.; Linck, C. F.; Zoeren, C. V.; Fox, B. B.; Mahaffy, P. G. J. Chem. Ed. 1985, 62, 519–521 and references cited therein.

2. A 10 mL acetic acid solution containing 0.10 M 5-nonanol, 0.10 M substituted 1-phenylethanol and 0.10 M chlorobenzene was divided into two 5.0 mL aliquots. One aliquot was stirred with 0.70 mL bleach at 21°C for 30 min. Both aliquots were worked up by adding 10 mL of water and 10 mL of CH2Cl2. The CH2Cl2 layer was separated and washed with 10% aqueous sodium carbonate. Relative areas were measured by GC and relative reactivities were calculated by krel=log (rel. area At/rel. area A0)/log (rel. area Bt/rel. area B0) where A is substituted 1-phenylethanol and B is 5-nonanol.

3. The relative reactivity was corrected by kcorr=krel/[1+(rel. area of ring chlorinated compounds)/(rel. area of ketone)].

4. (a) Lee, G. A.; Freedman, H. H. Isr. J. Chem. 1985, 26, 229–234.

5. (b) Mirafzal, G. A.; Lozeva, A. M. Tetrahedron Lett. 1998, 39, 7263–7266.

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