Efficient synthesis of 2,3-trans-tetrahydropyrans and oxepanes: Rearrangement-ring expansion of cyclic ethers having a chloromethanesulfonate
โ Scribed by Nobuyuki Hori; Kazuo Nagasawa; Takeshi Shimizu; Tadashi Nakata
- Book ID
- 104260932
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 249 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
Zn(OAc)2-treatment of cyclic ethers having a chloromethanesulfonate as an efficient leaving group on the side chain effected a stereoselective rearrangement reaction to give the ring-expanded ethers, 2,3-trans-tetrahydropyrans and oxepanes, in good yield.
๐ SIMILAR VOLUMES
Exo-trigonal-type intramolecular ring closure of the cf,8-epoxy sulfoxides with hvdroxvl group cave 2-acvl cyclic ethers (5. 6. and 13 membered rings) in good-yields.- In contrast to this, endo-trigonalltype ring closure of the a,8-epoxy sulfoxides was rather difficult. Recently, cyclic ethers hav