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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.