Halogeno-1,4-dioxans and their derivatives. Part IV. Some 2,3-disubstituted cis-1,4,5,8-tetraoxadecalins
Abstract
Reaction of trans-2,3-dichloro-1,4-dioxan with dimethyl (+)-tartrate yields dimethyl (–)-1,4,5,8-tetraoxadecalin-2,3-dicarboxylate in which the ring fusion is cis. The diethyl ester has been obtained similarly, and the dihydrazide and a monoamide monoethyl ester have been prepared.
The assignment of the ring-fusion as cis in these compounds is made from n.m.r. studies at 100 MHz.