Molecular rearrangements with thiol ester group migration. S-Phenyl (E)- and (Z)-2,3-diphenylthiolglycidates

Reactions of esters with phosphorus ylides. 3. Direct conversion into branched olefins

“…10 The results are summarized in Table I. The presence of strongly electron-withdrawing substituents (2-benzo [6]furyl-, 4pyridyl-11 *******) leads to a sharp decrease in olefin formation.…”

“…2.31 (s, 3, -CH3), 2.14 (s, 3, -CH3) 7.27 (d, 2,</ = 9 Hz, arom), m -methoxy phenyl ethyl A Me2SO m -methoxyisopropenylbenzene 73 6.71 (d, 2,J=9 Hz, arom), 5.25 (s, 1, =CH), 4.92 (s, 1, =CH), 3.62 (s, 3, -OCH3), 2.10 (s, 3, -CH3) 7.24-6.68 (m, 4, arom), 5.29 (s, 1, =CH), 5.03 o-methoxyphenyl ethyl B Me2SO o-methoxyisopropenylbenzene 78 (s, 1, =CH), 3.75 (s, 3, -OCH3), 2.13 (s, 3, -ch3) 7.18-6.68 (m, 4, arom), 5.12 (s, 1, =CH), 5.04 p-( dimethylamino )pheny 1 ethyl C Me2SO p-( dimethylamino )isopropenylbenzene 66 (s, 1, =CH), 3.81 (s, 3, -OCH3), 2.15 (s, 3, -ch3) 7.31 (d, 2, J = 8 Hz, arom), 6.61 (d,…”

“…The total yield was obtained as the sum of the yields of the identified constituents. 6 Also, 31% of fert-butyl benzoate was formed. a thermal conductivity detector using a 6 m, 20% SE-30, Chromosorb W 60-80 column.…”

“…XIII. 6 The total yield was obtained as the sum of the yields of the identified constituents. The total yield was obtained as the sum of the yields of the identified constituents.…”

“…The formation of appreciable amounts of enol ether in the case of ethyl formate is not unexpected. 6 Reaction of esters with the ylide from 5-(triphenylphosphonio)pentanoic acid (2 equiv of sodium hydride), a much used reagent in prostaglandin synthesis,18 gives rise to the formation of 5-substituted 4-nonene-l,9-dicarboxylic acids, which can only be extracted from the reaction mixture with great difficulty. Reaction of the disodium dicarboxylates in situ with an excess of methyl iodide, however, provides the dimethyl esters in good yields.…”