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Jump rope rotation in trans-cycloalkenes
- Source :
- Tetrahedron. 42:1703-1709
- Publication Year :
- 1986
- Publisher :
- Elsevier BV, 1986.
-
Abstract
- A series of 1,2-bis-methylenecycloalkane monoepoxides(2a-e)was prepared from the related 12-to 16-membered cyclic ketones. Reduction with lithium in ammonia afforded the corresponding trans-and cis-2-methylcycloalkenylmethanols (3a/4a-3e/4e) in ratios of 92:8-78:22. Sharpless epoxidation of these allylic alcohols with 0.6 equivalents of the reagent prepared from titanium isopropoxlde, (+)-diisopropyl tartrate, and t-butylhydroperoxide gave rise to a mixture of the epoxy alcohols 6a-e and recovered allylic alcohols. In the case of the 12- to 14-membered cycloalkenes the recovered alcohols 3a-c were optically active. The 15- and 16-membered cases 3d and e were racemic. Barriers to jump rope rotation were calculated by means of the Still Macro Model program.
Details
- ISSN :
- 00404020
- Volume :
- 42
- Database :
- OpenAIRE
- Journal :
- Tetrahedron
- Accession number :
- edsair.doi...........b0966af376df38da4c069edf6cc68710