✦ LIBER ✦
Transformation of [6] and [7]metacyclophanols into new strained tricyclic ethers via an intramolecular version of the SN2 reaction
✍ Scribed by Woo Song Lee; Yoshimitsu Nagao
- Book ID
- 104256963
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 229 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Treatment of 2a, b with LiAIH 4 gave the [61 and [7]metacyclophanols 4 and8 in good yields. The reactions of 4 and 8 with MeSO2CI in the presence of Et3N in CH2CI 2 rapidly proceeded to give the corresponding strained tricyclic ethers 6 and 10 via an intramolecular version of the SN2 reaction. This stereospecific cyclic ether formation in the mesylate molecules 5 and 9 can he rationalized in terms of a short nonbonded length between both reaction centers and a fairly rigid linear relationship between the leaving group and the nucleophilic group.