Tetrahedron

The preparation of substituted 3, 4-dihydro-l (2H)-naphthalenones from benzocyclobutenones via sequential thermal electrocyclic reactions

DN Hickman, KJ Hodgetts, PS Mackman, TW Wallace…

Index: Hickman, Derek N.; Hodgetts, Kevin J.; Mackman, Peter S.; Wallace, Timothy W.; Wardleworth, J. Michael Tetrahedron, 1996 , vol. 52, # 6 p. 2235 - 2260

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Citation Number: 26

Abstract

1-Alkenylbenzocyclobutenols, prepared from benzocyclobutenones via the addition of alkenyl Grignard reagents or the addition of alkynyllithium reagents followed by (E)-selective reduction, undergo successive thermal 4π and 6π electrocyclisations to give substituted 3, 4- dihydro-1 (2H)-naphthalenones. An analogous sequence gave 3, 4,-dihydro-1 (2H)- anthracenone from naphtho [b] cyclobuten-1 (2H)-one.

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