Photoinduced rearrangement of carbocyclic 2-phenylthio-1,3-diols to deoxysugars
✍ Scribed by Denis Gravel; Luc Farmer; Réal C. Denis; Erwin Schultz
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- French
- Weight
- 300 KB
- Volume
- 35
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
Irradiation of 1-(o-tolyl)-3,4-benzobicyclo[3.1.0]hexenones (1) in benzene at 365 nm has resulted in clean conversion to 3-(o-tolyl)-1-naphthols (2) via 3-(o-tolyl)-1(2H)-naphthalenones. The reaction is suggested to occur mainly from (n, p\*) 3 state with a reaction rate higher than 10 10 s -1 .
This paper reports the regioselective photorearrangement of 2-phenylthio-3-aminocyclohexanols to deoxyazasugars and their derivatives. These give access to variously substituted piperidines, amino-sulfones, -sulfoxides and -acids.
The [1,2] Wittig rearrangement of P-alkoxyalkyl ally1 ethers has been studied and found to provide syn-1,3-diol derivatives in 14-32% yield and with useful levels of diastereoselection. The rearrangement of a-metalated ethers (Wittig rearrangement) has been of interest to investigators since its di