High diastereoselectivity in the cyclization of 1,5-biradicals: what causes such sizeable steric barriers to biradical coupling?

Peter J. Wagner; Bong Ser Park

doi:10.1016/0040-4039(91)80844-V

High diastereoselectivity in the cyclization of 1,5-biradicals: what causes such sizeable steric barriers to biradical coupling?

Peter J. Wagner, Bong Ser Park

Department of Chemistry

Michigan State University

Research output: Contribution to journal › Article › peer-review

16 Scopus citations

Abstract

The high diastereoselectivites observed in the photocyclization of α-(o-ethylphenyl)acetophenones appear to reflect conformational equilibria in the triplet 1,5-biradical intermediates rather than steric barriers created during cyclization. The necessary biradical triplet→singlet intersystem crossing is proposed to occur along the cyclization reaction coordinate since the orthogonality of the two singly-occupied p orbitals does not depress biradical lifetimes.

Original language	English
Pages (from-to)	165-168
Number of pages	4
Journal	Tetrahedron Letters
Volume	32
Issue number	2
DOIs	https://doi.org/10.1016/0040-4039(91)80844-V
State	Published - 7 Jan 1991

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abstract = "The high diastereoselectivites observed in the photocyclization of α-(o-ethylphenyl)acetophenones appear to reflect conformational equilibria in the triplet 1,5-biradical intermediates rather than steric barriers created during cyclization. The necessary biradical triplet→singlet intersystem crossing is proposed to occur along the cyclization reaction coordinate since the orthogonality of the two singly-occupied p orbitals does not depress biradical lifetimes.",

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AB - The high diastereoselectivites observed in the photocyclization of α-(o-ethylphenyl)acetophenones appear to reflect conformational equilibria in the triplet 1,5-biradical intermediates rather than steric barriers created during cyclization. The necessary biradical triplet→singlet intersystem crossing is proposed to occur along the cyclization reaction coordinate since the orthogonality of the two singly-occupied p orbitals does not depress biradical lifetimes.

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High diastereoselectivity in the cyclization of 1,5-biradicals: what causes such sizeable steric barriers to biradical coupling?

Abstract

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