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Thermal Pericyclic Tandem Reactions
Author(s) -
Hopf Henning,
Wolff Joachim
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200111)2001:21<4009::aid-ejoc4009>3.0.co;2-4
Subject(s) - pericyclic reaction , chemistry , tandem , claisen rearrangement , pyrolysis , computational chemistry , hydrogen , organic chemistry , materials science , composite material
Gas phase thermal isomerizations of twelve acetylenic systems, all of which can in principle undergo two successive pericyclic steps, are described. The substrates, the syntheses and spectroscopic properties of which are presented, are formal derivatives of but‐2‐yne, with different functional groups in the 1‐ and the 4‐positions. The Cope, Claisen, Claisen ester, retro‐ene, 1,5‐hydrogen shift, and 1,5‐homo hydrogen‐shift processes were employed as the pericyclic steps from which the tandem processes were composed. The compositions of the pyrolysates obtained were determined over broad temperature ranges, and the mechanisms of the individual steps producing the pyrolysis products are discussed.