Kinetically controlled nucleophilic addition-reactions to methyl 4,6-O-benzylidene-2,3-dideoxy-2-nitro-α-d-erythro-hex-2-enopyranoside
✍ Scribed by Tohru Sakakibara; Yoshifusa Tachimori; Rokuro Sudoh
- Book ID
- 107725449
- Publisher
- Elsevier Science
- Year
- 1984
- Tongue
- English
- Weight
- 851 KB
- Volume
- 131
- Category
- Article
- ISSN
- 0008-6215
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## Nucleophilic addition-reactions of the title compound, prepared from the corresponding 3-nitrohex-2-enitol, were investigated under kinetically controlled conditions; such sterically bulky nucleophiles as tert-butyl peroxide and 2,4-pentanedionate ions (except in 1,Cdioxane) were found to enga
IZUMI TAKAI, YOSHIFUSA TACHIMORI, AZUMA YAMAMOTO, YOSHIHARU ISHIDO\*, AND (the late) ROKURO SUWH
Reactions of the title compounds with several nucelophiles suggested that the ring oxygen atom (0-5) accelerated the reactivity of the nitro alkene moiety, but scarcely affected the stereoselectivity of the nucleophilic attack.