Under kinetic control, the reaction of o-thioquinones with acyclic 1,3-dienes afforded, as main products, the spiro cycloadducts deriving from the participation of the thiones as dienophiles. Under thermodynamic control, or with cyclic dienes, the thioquinones behave as hetero dienes to give the benzoxathiin derivatives with complete regioselectivity.
[2+4] VS. [4+2] CYCLOADDITION REACTIONS OF o-THIOQUINONES WITH 1,3-DIENES / S. Menichetti; C. Viglianisi. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 59:(2003), pp. 5523-5530. [10.1016/S0040-4020(03)00811-1]
[2+4] VS. [4+2] CYCLOADDITION REACTIONS OF o-THIOQUINONES WITH 1,3-DIENES
MENICHETTI, STEFANO;VIGLIANISI, CATERINA
2003
Abstract
Under kinetic control, the reaction of o-thioquinones with acyclic 1,3-dienes afforded, as main products, the spiro cycloadducts deriving from the participation of the thiones as dienophiles. Under thermodynamic control, or with cyclic dienes, the thioquinones behave as hetero dienes to give the benzoxathiin derivatives with complete regioselectivity.
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