Synthesis and reactivity of (1-fluorovinyl) phenyl sulfoxide as a dienophile

(1-Fluorovinyl) phenyl sulfoxide 2 was prepared in two steps from (1-fluorovinyl)methyldiphenylsilane. Although the sulfoxide 2 underwent Diels-Alder reaction with very reactive diene, 1,3-diphenylisobenzofuran, to give the corresponding fluorinated-naphthalene derivative in one step, it did not afford cycloadducts with other dienes employed.