Stereochemistry of the Diels–Alder reaction: effect of diene structure on endo-selectivity
- 1 January 1974
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 1,p. 22-25
- https://doi.org/10.1039/p29740000022
Abstract
Structures are assigned to adducts of cyclohexa-1,3-diene and spiro[2,4]hepta-1,3-diene with a number of dienophiles. Product ratios are determined, results are compared with reactions of cyclopentadiene, and it is concluded that the major steric interaction which controls endo-selectivity is that between substituents of the dienophile and the methylene hydrogens of cyclopentadiene and of cyclohexa-1,3-diene, and the methylene group of spiro[2,4]hepta-1,3-diene.Keywords
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