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Efficient synthesis of 2,3-trans-tetrahydropyrans and oxepanes: Rearrangement-ring expansion of cyclic ethers having a chloromethanesulfonate

โœ 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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โœฆ 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.


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โœ Tsuyoshi Satoh; Ken-ichi Iwamoto; Koji Yamakawa ๐Ÿ“‚ Article ๐Ÿ“… 1987 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 231 KB

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