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Photolysis of heptanal

Journal of Organic Chemistry, ISSN: 0022-3263, Vol: 71, Issue: 17, Page: 6403-6408
2006
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Article Description

Photolysis of heptanal is investigated from an experimental and theoretical point of view. Photoexcited heptanal is believed to undergo rapid intersystem crossing to the triplet manifold and from there undergoes internal H-abstraction to form biradical intermediates. The favored γ-H abstraction pathway can cyclize or cleave to 1-pentene and hydroxyethene, which tautomerizes to acetaldehyde. Yields of 1-pentene and acetaldehyde were measured at 62 ± 7% and 63 ± 7%, respectively, relative to photolyzed heptanal. Additionally, small quantities of hexanal and hexanol were observed. On the basis of combined experimental and theoretical evidence, the remaining heptanal photolysis proceeds to form an estimated 10% HCO + hexyl radical and 30% cyclic alcohols, particularly 2-propyl cyclobutanol and 2-ethyl cyclopentanol. © 2006 American Chemical Society.

Bibliographic Details

Suzanne E. Paulson; De Ling Liu; Grazyna E. Orzechowska; Luis M. Campos; K. N. Houk

American Chemical Society (ACS)

Chemistry

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