140837-20-3Relevant academic research and scientific papers
Tuning of vinylborane dienophilicity. Optimization of reactivity, regioselectivity, endo stereoselectivity, and reagent stability
Singleton, Daniel A.,Martinez, Jose P.,Watson, Jose V.,Ndip, Grace M.
, p. 5831 - 5838 (2007/10/02)
Simple syntheses of some vinylboranes are reported, and their properties in Diels-Alder reactions are compared. Vinyl-3,6-dimethylborepane was the most stable simple vinylborane examined, and appears to be indefinitely stable at 25°C. Surprisingly, trivinylborane is the most reactive, and reacts about 18 times faster than the vinyldialkylboranes with cyclopentadiene. Vinyl-9-BBN is the most regioselective dienophile, in keeping with principally steric control of regioselectivity in Diels-Alder reactions of vinylboranes. All the dienophiles display high endo-stereoselectivity with piperylene, but vinyl-3,6-dimethylborepane displays significantly improved stereoselectivity with cyclopentadiene. In general, by choice of alkyl-substituents on boron, the reactivity, regioselectivity, endo-stereo selectivity, and stability of vinylboranes can be optimized.
Vinylboranes are Omniphilic Dienophiles. Some Unusual and Useful Properties of Vinylboranes in Diels-Alder Reactions
Singleton, Daniel A.,Martinez, Jose P.,Watson, Jose V.
, p. 1017 - 1020 (2007/10/02)
The rate of Diels-Alder reactions with vinyl-9-BBN is uniquely insensitive to diene substituent effects, and high reactivity is observed with both electron-rich and electron-poor dienes.The regioselectivity of these reactions is controlled mainly by steric effects.
