The Diels-Alder Reactions of 6,6-Dimethoxycyclohexa-2,4-dienone Generated by Pyrolysis of its Dimer

Abstract

The MOB 2 generated in situ by the pyrolysis of its dimer 3 participated in Diels-Alder reactions with various olefinic and acetylenic dienophiles at 220 °C to provide bicyclo[2.2.2]octenones and bicyclo[2.2.2]octadienones, respectively. Reactions proceeded with high degree of regio- and stereoselectivity.

Key words

2-methoxyphenols - masked o-benzoquinones - retro-Diels-Alder reaction - Diels-Alder reaction - domino reactions

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6

Liao, C.-C.; Peddinti, R. K. Acc. Chem. Res. manuscript submitted.

17

Lai, C.-H.; Shen, Y.-L.; Rao, N. S. K.; Wang, M.-N.; Ko, S.; Liao, C.-C. in preparation.

20

Chuang, J.; Liao, C.-C. unpublished results.

22

Chen, A.-C.; Liao, C.-C. unpublished results.