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Chlorination of 1,5-anhydro-3-nitro-1-enitol derivative in various ethers and its mndo study

โœ Scribed by Tohru Sakakibara; Kohji Yoshino; Hiroyuki Iizuka; Yoshiharu Ishido

Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
259 KB
Volume
27
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Chlorination of 3-nitro-P-glucal derivative in ethylene oxide and in hexamethylene oxide is described and compared with those in p-dioxane, tetrahydrofuran, tetrahydropyran, trimethylene oxide, and diethyl ether; a fairly good correlation is observed between the yield of Q-glucopyranosyl chloride (4) and methyl cation affinity.

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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.

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The cyclopolymerization of 3,4-di-O-allyl-1,2 : 5,6-dianhydro-D-mannitol ( 1) was carried out using BF 3 rOEt 2 and t-BuOK. The polymer obtained by the polymerization with BF 3 rOEt 2 mainly consisted of (1r6)-bonded 3,4-di-O-allyl-2,5-anhydro-Dglucitol as the five-membered constitutional repeating