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Site selective cycloaddition reaction of 1 -methoxy- 1-trimethylsiloxy-1,3,5-hexatriene with dienophile

✍ Scribed by Masatomi Ohno; Kohki Mori; Shoji Eguchi

Book ID
104218881
Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
220 KB
Volume
27
Category
Article
ISSN
0040-4039

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✦ Synopsis

The Diels-Alder reaction of the title triene occurred at the site of C-3-C-6 rather than of intuitively favored C-l-C-4, as the result of the prevailing steric effect over the orbital effect.

πŸ“œ SIMILAR VOLUMES

Cycloaddition reactions of heteroazadien
Cycloaddition reactions of heteroazadienes: [4+2] cycloaddition of 1-thia-3-azabutadienes with electron-poor dienophiles
✍ JosΓ© Barluenga; Miguel TomΓ‘s; Alfredo Ballesteros; Luis A. LΓ³pez πŸ“‚ Article πŸ“… 1989 πŸ› Elsevier Science 🌐 French βš– 209 KB

Summmy. 1-Thia-3-azabutadienes cleanly undergo [4 + 21 cycloaddition processes with electron-poor dienophiles; the reaction is regioselective and leads exclusively to the endo isomer.