
TY  - JOUR
A1  - Cherry, WH 
A1  - Porter, QN 
T1  - Vinylindenes and Some Heteroanalogues in the Diels-Alder Reaction, VII. Vinylbenzo[b]thiophens and 1,4-Naphthoquinone
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1979
VL  - 32
IS  - 1
SP  - 145
EP  - 151
KW  - 
UR  - https://doi.org/10.1071/CH9790145 
N2  - A mechanism postulated for the base-catalysed oxidative rearrangement of 5,5a,6,12a,12b,13-hexa-hydroanthra[l,2-b]benzo[d]thiophen-5,13-dione (the adduct of 3-vinylbenzo[b]thiophen and 1,4-naph-thoquinone) to anthra[2,3-b]benzo[d]thiophen-7,12-quinone is supported by isolation of a 5a,6-di-hydro derivative when the reaction is carried out in the absence of oxygen. Similar derivatives are formed from two methyl homologues of the adduct. Conditions are described for conversion of the adducts into 6,7-dihydroanthra[l,2-b]benzo[d]thiophen-5,13-quinones, and it is also shown that 2-methyl-3-vinylbenzo[b]thiophen and 1,4-naphthoquinone give an adduct in which the diene has undergone isomerization before adduct formation. 
ER  -

