The reaction of 4-hydroxy[2.2]paracyclophane with phthalimidesulfenyl chloride allowed the preparation of a suitable precursor for a paracyclophane-o-thioquinone. This species participates in an inverse electron demand hetero Diels–Alder reaction with different electron-rich alkenes to give the expected benzoxathiin cycloadducts with complete control of regio- and stereochemistry
o-Thioquinones on [2,2]paracyclophanes: an example of totally stereocontrolled hetero Diels-Alder reactions / S. Menichetti; C. Faggi; G. Lamanna; A. Marrocchi; L. Minuti; A. Taticchi. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 62:(2006), pp. 5626-5631.
o-Thioquinones on [2,2]paracyclophanes: an example of totally stereocontrolled hetero Diels-Alder reactions
MENICHETTI, STEFANO
;FAGGI, CRISTINA;
2006
Abstract
The reaction of 4-hydroxy[2.2]paracyclophane with phthalimidesulfenyl chloride allowed the preparation of a suitable precursor for a paracyclophane-o-thioquinone. This species participates in an inverse electron demand hetero Diels–Alder reaction with different electron-rich alkenes to give the expected benzoxathiin cycloadducts with complete control of regio- and stereochemistryFile | Dimensione | Formato | |
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