Tetrahedron letters

PCC-mediated novel oxidation reactions of homobenzylic and homoallylic alcohols

RA Fernandes, P Kumar

Index: Fernandes, Rodney A.; Kumar, Pradeep Tetrahedron Letters, 2003 , vol. 44, # 6 p. 1275 - 1278

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Citation Number: 29

Abstract

A new PCC-mediated carbon carbon bond cleavage reaction during oxidation of homobenzylic alcohols leading to the formation of benzylic carbonyl compounds has been observed. Homobenzylic alcohols with no benzylic substitution (R1= H) gave benzylic aldehydes without further oxidation, while those with benzylic substitution (R1= Me, Et, Ar) gave benzylic ketones. In contrast, homoallylic alcohols gave products arising from double ...

~68%

~61%

~70%

~64%

~66%

~63%

~64%

~72%

~64%

~70%

~72%

~61%

~63%

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