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Synthesis of Norbornenes from Cyclopentadiene and Allyl Alcohols in an Acidic Two Phase System
Author(s) -
Ernst née Vathke Heidrun,
Hoffmann H. M. R.
Publication year - 1980
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.198008271
Subject(s) - cyclopentadiene , substituent , chemistry , allyl alcohol , pentane , medicinal chemistry , organic chemistry , catalysis
A novel stepwise Diels‐Alder type mechanism can be postulated for the reaction of the allyl alcohol (1) with cyclopentadiene in TsOH/pentane. An allyl cation (2) without donor‐substituent on the central C atom functions as “dienophile”. Substituted cyclopentenols accompany (3) .
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