6533b820fe1ef96bd1279903

RESEARCH PRODUCT

Generation of hexahydroazulenes

Herbert MeierHeiner DetertGuido Krämer

subject

chemistry.chemical_compoundchemistryFlash vacuum pyrolysisBicyclic moleculeStereochemistryOrganic ChemistryDrug DiscoveryStructural isomerAlcoholConjugated systemRing (chemistry)BiochemistryMedicinal chemistry

description

(Z)-Cyclodec-1-en-6-yne (3) generates three conjugated hexahydroazulenes 3→1k→1c, 1l under FVP conditions, whereas flash vacuum pyrolysis (FVP) of cyclodecyne (2) leads to 1,2,9-decatriene (9). We attribute the different thermal behavior of 2 (ring opening) and 3 (ring closure) to different transannular interactions. Altogether 22 constitutional isomers of hexahydroazulene should exist; three new isomers (1k, 1l, and 1m) are presented here, ten were described earlier, but the reinvestigation of the dehydration route of bicyclic alcohol 11 showed that one of the ten structures has to be revised.

yearjournalcountryeditionlanguage
2009-08-01Tetrahedron Letters
https://doi.org/10.1016/j.tetlet.2009.05.025