Restricted Rotation Involving the Tetrahedral Carbon. I. Some Diels-Alder Adducts Derived from 9-Substituted Anthracenes

Ring-Opening of Hetero-Diels--Alder Adducts

Thermally cleavable surfactants based on furan-maleimide Diels-Alder adducts.

Two new surfactant molecules are reported that contain thermally labile Diels-Alder adducts connecting the hydrophilic and hydrophobic sections of each molecule. The two surfactants possess identical hydrophobic dodecyl tail segments but have phenol and carboxylic acid hydrophilic headgroups, respectively. Deprotonation with potassium hydroxide affords the formation of water-soluble surfactants...

Hetero-Diels-Alder reactions of new sulfonylsulfines generated from α-substituted methylsulfones

Hetero-Diels-Alder reaction with sulfines generated in situ from methylsulfones 5a-e substituted in α-position with a phosphonyl, carboxyl, carboxyoxazolidinyl, pyridyl, or a quinolyl substituent, respectively, led to new highly functionalized thiopyrans cycloadducts. When in the substrates (i.e. 5a-c) the sulfonyl group and the second substituent on the methylene carbon have comparable electro...

Synthetic studies towards the mulberry Diels-Alder adducts: H-bond accelerated cycloadditions of chalcones.

The methyl ether derivatives 2, 4 and 6 of the mulberry Diels-Alder adducts chalcomoracin (1) and mulberrofuran C (3) and kuwanon J (5) respectively have been synthesized by a thermal [4 + 2]-cycloaddition reaction between a chalcone and dehydroprenyl diene. A H-bonded ortho OH substituent on the chalcone was found to be essential for Diels-Alder reactivity. Density functional theory calculatio...

Appendix 1. Diels-Alder Reactions

One of the most efficient methods (high yield, controlled stereochemistry, diverse functionality) to construct rings from smaller fragments is via cycloaddition reactions. The reverse reaction, namely splitting of a ring into smaller fragments is termed a cycloreversion reaction is also an important synthetic tool. (For example, in the present experiment it is the cracking of cyclopentadiene di...