Tetrahedron

The behavior of the singlet and triplet spin states of methylene-bridged 1, 8-naphthoquinodimethane with O 2

RM Pagni, MN Burnett, HM Hassaneen

Index: Pagni, Richard M.; Burnett, Michael N,; Hassaneen,Hamdi M. Tetrahedron, 1982 , vol. 38, # 6 p. 843 - 851

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Citation Number: 9

Abstract

It has been shown that thermolysis of naphthocyclopropane 8 yields the singlet 1, 8- naphthoquinodimethane 7 by disrotatory ring opening. In fluid solution the singlet biradical prefers to ring close to regenerate the starting material rather than under a 1, 2-hydrogen shift to yield phenalene (9). It has been demonstrated that the singlet 7 does not react with O2 or undergo intersystem crossing to ground state triplet 7. It has also been shown by an ...