2008
DOI: 10.1002/hlca.200890240
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Photocycloaddition Reactions of 2‐(Alk‐3‐en‐1‐ynyl)cyclohex‐2‐enones

Abstract: The newly synthesized 2-(alk-3-en-1-ynyl)cyclohex-2-enones 4 undergo photodimerization (chemoand regio-)selectively at the exocyclic C¼C bond to give diastereoisomeric mixtures of 1,2-dialkynyl-1,2-dimethylcyclobutanes. On irradiation of 4 in the presence of 2-chloroacrylonitrile, cyclobutane formation occurs again (chemo-and regio-)selectively at the exocyclic C¼C bond to afford diastereoisomeric mixtures of 2-alkynyl-1-chloro-2-methylcyclobutanecarbonitriles. Similarly, compounds 4 undergo photoaddition to 2… Show more

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Cited by 6 publications
(2 citation statements)
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“…Although a major focus of their work was on possible shifts of the spin centers in triplet intermediates (leading to products which are beyond the scope of this review), several enones also delivered conventional [2 + 2] photocycloaddition products. In Figure , some of the enones 189 – 196 are summarized which were investigated in the last two decades. Compounds which exhibit a chemoselectivity preference in favor of [2 + 2] photocycloaddition products are drawn in black, compounds which followed mainly non-[2 + 2] pathways are shown in gray. Enones with a heteroatom in the ring are discussed in section .…”
Section: Direct Excitation and Sensitizationmentioning
confidence: 99%
“…Although a major focus of their work was on possible shifts of the spin centers in triplet intermediates (leading to products which are beyond the scope of this review), several enones also delivered conventional [2 + 2] photocycloaddition products. In Figure , some of the enones 189 – 196 are summarized which were investigated in the last two decades. Compounds which exhibit a chemoselectivity preference in favor of [2 + 2] photocycloaddition products are drawn in black, compounds which followed mainly non-[2 + 2] pathways are shown in gray. Enones with a heteroatom in the ring are discussed in section .…”
Section: Direct Excitation and Sensitizationmentioning
confidence: 99%
“…Quite recently it has been shown that radical anions of arylenones generated by PET from suitable Ru complexes cycloadd to aliphatic Michael acceptors affording 1,2-diacylcyclobutanes . The behavior of enynones 1 parallels that of cross-conjugated 2-(alkenynyl)cyclohex-2-enones 15 , in reactions with conjugated alkenes by affording cyclobutanes efficiently via chemoselective primary binding at the olefinic terminus of the enyne system. This indicates that these (triplet) excited enynones behave like cummulenic biradicals 16 / 17 exhibiting a high spin density on the enyne olefinic terminus (Scheme ).…”
mentioning
confidence: 99%