The conformational analysis of saturated heterocycles. Part LXVII. 2-Alkyl-3,6-dihydro-2H-1,2-oxazines and 3-alkyl-3,4-dihydro-1H-2,3-benzoxazines
- 1 January 1974
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 14,p. 1737-1741
- https://doi.org/10.1039/p29740001737
Abstract
Low temperature n.m.r. studies of the title compounds indicate that nitrogen inversion is slowed. Peak area measurements show that 2-methyl substituents prefer the equatorial position by a factor of ca. 10 : 1 and 2-t-butyl substituents by a considerably larger factor. This considerable equatorial preference is due in part to lone pair–lone pair repulsion in the 2-axial conformers. The conclusions from n.m.r. are compared with measured and calculated dipole moments.Keywords
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