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Stereoselective Cyclopropane Syntheses by “Oxy‐Homodienyl Hydrogen Shifts”
Author(s) -
Klärner FrankGerrit,
Rüngeler Wolfgang,
Maifeld Werner
Publication year - 1981
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198105951
Subject(s) - cyclopropane , stereoselectivity , chemistry , diene , hydrogen , stereochemistry , computational chemistry , medicinal chemistry , organic chemistry , catalysis , ring (chemistry) , natural rubber
The stereoselective rearrangement of hexadienols (1) into cyclopropylacetaldehydes (2) , R 4 = H, or cyclopropylmethyl methyl ketones (2) , R 4 = CH 3 , takes place by “oxy‐homodienyl hydrogen shift”. In the case of the corresponding hydrocarbons the equilibrium is on the side of the acyclic diene.