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Studies on the Synthesis of Tetrahydrofuran and ‐pyran Derivatives from Terpenes, III. Conversion of cis ‐2‐[3‐(2‐Hydroxypropyl)‐2,2‐dimethylcyclopropyl]ethanol to THF and THP Derivatives
Author(s) -
Podlejski Jerzy,
Kula JÓSef
Publication year - 1989
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198919890183
Subject(s) - chemistry , tetrahydrofuran , yield (engineering) , diol , ethanol , sulfuric acid , organic chemistry , terpene , medicinal chemistry , solvent , materials science , metallurgy
Sulfuric acid‐catalyzed reaction of cis ‐diol 1 leads to a mixture of four heterocyclic alcohols 2–5 , which after oxidation yield a mixture of carbonyl compounds 6–9 . These compounds were separated and their structures were determined on the basis of spectral data and GC analysis. It was found that THF deriatives ( 2 and 4 ) are the main rearrangement products of diol 1 , and their high percent ratio in the mixture is discussed as a result of thermodymamic equilibrium between THF ( 2, 4 ) and THP ( 3, 5 ) derivatives.