85972-31-2Relevant academic research and scientific papers
THE DIELS-ALDER REACTIVITY OF SOME NEW SULFUR (SELENIUM) SUBSTITUTED HALOBUTADIENES
Bridges, Alexander J.,Fischer, John W.
, p. 447 - 450 (1983)
3-PhS(e)-(1),2-(di)halobutadienes undergo BF3 catalysed cycloadditions with methyl vinyl ketone at 25 deg C, to give good yields of adducts in which the regiochemistry of addition is mainly controlled by the sulfur (selenium) atom.
Preparation and Diels-Alder Reactivity of Several New Chalcogen-Halogen Substituted Butadienes
Bridges, Alexander J.,Fischer, John W.
, p. 2954 - 2961 (2007/10/02)
Addition of halogens and pseudohalogens across one ?-bond of 1,4-dichlorobut-2-yne, followed by a 1,4-elimination, is an efficient synthesis of several new polysubstituted butadienes.If the product dienes have a sulfur or selenium substituent they are quite reactive, undergoing cycloaddition with the moderately reactive dienophile methyl vinyl ketone at 20 deg C in the presence of boron trifluoride etherate.The regiochemistry of the cycloadditions was elucidated, and the limitations of the methodology are discussed.
