cis-3,5-Cyclohexadiene-1,2-diol derivatives: facial selectivity in their Diels-Alder reactions with ethylenic, acetylenic and azo dienophiles
Date
2006
Authors
Ogbomo, Sunny M.
Burnell, D. Jean
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Abstract
The Diels - Alder reactions of maleimide with the acetonide derivative (6a) of
cis-3,5-cyclohexadiene-1,2-diol (1a) in various solvents showed facial selectivities ranging from 1
: 1 to 1 : 9. The same derivative 6a reacted in benzene with ethylenic dienophiles with generally
modest facial selectivity, but acetylenic dienophiles added exclusively anti to the oxygen functions
of 6a. Dimerization of cyclic acetals 6a and 7 was mainly, but for 6a not exclusively, by anti
addition with respect to both the diene and the dienophile partners. Reactions of azo dienophiles
with derivatives of 1a were predominantly by anti addition, but the diol itself ( 1a) gave the syn
adduct as the major product.
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Citation
Ogbomo, Sunny M., and D. Jean Burnell. 2006. "cis-3,5-Cyclohexadiene-1,2-diol derivatives: facial selectivity in their Diels-Alder reactions
with ethylenic, acetylenic and azo dienophiles." Organic & Biomolecular Chemistry 4(20): 3838-3848.