Sulfur (Or Selenium)-Mediated Synthesis of Methanoanthracene Derivatives. The First Synthesis of a Seleno-Cyanohydrin

Abstract

A synthesis of thio- and seleno-substituted 9,10-dihydro-9,10-methanoanthracene derivatives is reported. They are obtained by Wittig rearrangement from 11-thia and 11-selena-9,10-dihydro-9,10-ethanoanthracene derivatives. This rearrangement is applied to the first synthesis of a seleno-cyanohydrin (R¹R²C(SeH)CN).

Key Words:

• 9,10-dihydro-9,10-methanoanthracene
• Wittig rearrangement
• seleno-cyanohydrine
• Diels-Alder adducts
• thioaldehydes
• anthracene derivatives.