Synthesis of Medium‐Size Macrocycles by Cinnamate [2 + 2] Photoaddition | Zendy

König Burkhard | Zendy; Leue Stefanie | Zendy; Horn Clemens | Zendy; Caudan Arnaud | Zendy; Desvergne JeanPierre | Zendy; BouasLaurent Henri | Zendy

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Synthesis of Medium‐Size Macrocycles by Cinnamate [2 + 2] Photoaddition

Author(s) -

König Burkhard,

Leue Stefanie,

Horn Clemens,

Caudan Arnaud,

Desvergne JeanPierre,

BouasLaurent Henri

Publication year - 1996

Publication title -

liebigs annalen

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0947-3440

DOI - 10.1002/jlac.199619960802

Subject(s) - chemistry , isomerization , chromophore , enediyne , yield (engineering) , double bond , photochemistry , aryl , stereochemistry , polymer chemistry , organic chemistry , catalysis , materials science , alkyl , metallurgy

Unsaturated macrocycles were obtained by [2 + 2] photoaddition of acyclic biscinnamates. The orientation of the chromophores by ortho ‐xylyl ( 2 ) or aryl‐1,2‐diynyl ( 6 ) spacers leads to the formation of photoproducts in solution as single stereoisomers in high yield. The analogous photocyclization of a cis ‐enediyne biscinnamate 4 was less efficient, because of a rapid photochemical isomerization of the central double bond.

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