Bis (1-propyny1) methanol (la), bis (phenylethyny1) methanol (lb), and tetrakis (l-propynyl) cthane-l, 2-diol (10) are highly activated propargyl alcohols. Because of their sensitivity to acid, conversions of 1 to carbamate, ester, ether, and halide best proceed under neutral or basic conditions. Even so, disruptions of the diyne system are common, eg, the formation of 4-bromo-2, 5-heptadiyne and 2-bromo-2, 3-heptadien-5-yne from la, thermal cleavage of ...
