
TY  - JOUR
A1  - Hewgill, FR 
A1  - Hewitt, DG 
A1  - Howie, GB 
A1  - Spencer, WL 
T1  - Oxidation of alkoxyphenols. XX. Ring cleavage and lactone formation in the oxidation of a Biphenyl-2,2'-diol by lead tetraacetate
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1977
VL  - 30
IS  - 9
SP  - 1971
EP  - 1978
KW  - 
UR  - https://doi.org/10.1071/CH9771971 
N2  - Two products in the lead tetraacetate oxidation of 3,3?-di-t-butyl- 5,5?-dimethoxybiphenyl-2,2?-diol have been shown to be (E)-7-t-butyl-5- methoxy-3-[(E)-2?-methoxy-5?,5?-dimethyl-4?-oxohex-2?- enylidenelbenzofuran-2(3H)-one (1) and its (Z,Z) isomer (3). Treatment of these with base causes rearrangement to (E)-8-t-butyl-2-(3?,3?- dimethyl-2?-oxobutylidene)-6-methoxy-2H-1-benzopyran-4-carboxylic acid (13). Further treatment with base produces pinacolone and 8-t-butyl-6- methoxy-2-oxo-2H-1-benzopyran-4-carboxylic acid (14). The latter has been synthesized from 2-t-butyl-4-methoxyphenol via 7-t-butyl-5- methoxy-2,3-dihydrobenzofuran-2,3-dione (15). 
ER  -

