Nuclear magnetic resonance experiments on acetals. Part LVIII. Conformational studies of 4-methylene-1,3-dioxan
- 1 January 1975
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 13,p. 1434-1438
- https://doi.org/10.1039/p29750001434
Abstract
Complete analysis of the 1H n.m.r. spectra of 4-methylene-(1), 2-methyl-4-methylene-(2), and 6-methyl-4-methylene-1,3-dioxan (3) clearly discloses substantial flattening in the C(2)–O(3)–C(4)–C(5)–C(6) region, but not in the C(6)–O(1)–C(2) region. A typical torsion angle set is proposed. The barrier to ring inversion in (1) is found to be 5.4 ± 0.3 kcal mol–1(Tc=–161° in Freon-21).Keywords
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