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Removal of Water - a Factor Influencing the Synthesis of Alkynes in a Phase-Transfer Catalyzed - beta - Elimination Reaction

Zakrzewski J., Huras B., Sas A., Żelechowski K., Bombińska D.

Polish Journal of Chemistry

2008

Vol. 82, nr 5

1051-1057

Acetylene derivatives 4 were synthesized from the corresponding vicinal bromo compounds 2 in the phase-transfer catalyzed hydrogen bromide - beta elimination reaction using solid potassium hydroxide as a base, xylene as a solvent, and a phase-transfer catalyst. The yields of the synthesized acetylene derivatives 4 were substantially improved when water formed in the process had been removed.

Reactivity and crystal structure of 1,2:3,4:5,6-Tri-O-isopropylidene-D-gluconolactone

Jarosz S., Ciunik Z.

Polish Journal of Chemistry

1998

Vol. 72, nr 7

1182-1190

1,2:3,4,5,6-Tri-O-isopropylidene-D-gluconate (1) undergoes the beta-elimination reaction in the presence of LDA to afford 3-deoxy-1,2:5,6-di-O-isopropylidene-D-erythro-hex-3-enolactone (6). Attempts to prepare the phosphonate 4 by reaction of 1 with dimethyl methylphosphonate in the presence of LDA failed; only elimination product 6 was isolated from the reaction mixture. The sugar phosphonate 8 (protected form of 4) was prepared from methyl 2-O-benzyl-3,4:5,6-di-O-isopropylidene gluconate (7) by reaction with (-)CH2P(O)(OMe)2. The crystal structure of 1 is reported.