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Δ3-Dihydropyrans and tetrahydropyrans by reduction of pyrylium salts with sodium borohydride in acetic acid

✍ Scribed by Teodor-Silviu Balaban; Alexandru T Balaban

Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
291 KB
Volume
28
Category
Article
ISSN
0040-4039

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✦ Synopsis

The major reduction products with triaeetoxyborohydride INaBH, in A&H) of 2,4,6--trisubstituted pyryZiwn salts bearing alkyd substituents in the 2-and/or 6-position are the L3-dihydropyrcvas with cis Z-and 6-substituents and the aZZ-cis-2,4,&trisubstituted -tetrahydropyrcms. A3-Dihydropyrms are sham to be formed via ZH-pyrons by a 1,4 reduction whii!e tetrahydropyrans result from 4H-pyrans by reduction of both enol-ether double bonds.

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Unexpected formation of 1,2-dihydro-2-az
Unexpected formation of 1,2-dihydro-2-azolyl-and azinylisoquinolines by the reduction of the corresponding isoquinolinium salts with sodium borohydride in methanol
✍ Ibolya Prauda; Mária Tóth-Lauritz; József Reiter 📂 Article 📅 2004 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 142 KB

## Abstract The reduction of different 2‐azolyl‐and azinylisoquinolinium salts with sodium borohydride in methanol was studied. Surprisingly, contrary to what is found in the literature 1,2‐dihydroisoquinoline derivatives were obtained. Their formation was attributed to the electron withdrawing cha