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Pyrolysis of Sulfones as a Synthetic Method [New synthetic methods (28)]
Author(s) -
Vögtle Fritz,
Rossa Ludovica
Publication year - 1979
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.197905151
Subject(s) - sulfone , pyrolysis , chemistry , ring (chemistry) , steric effects , heteroatom , cleavage (geology) , molecule , organic chemistry , polymer chemistry , materials science , fracture (geology) , composite material
Cyclic sulfoness containing structural elements such as aromtic rings, heteroatoms. functional groups, and further SO 2 ‐groups as ring members decompose on heating with cleavage of SO 2 and formation of a new CC bond. In the last decade this “sulfone pyrolysis” has been expanded into a generally applicable method even allowing the synthesis of sterically strianed medium‐membered and multi‐membered cyclic and polycyclic systems containing aromatic ring. By the pyrolysis of sulfones which are only unilateally activated by benzyl moieties, aromatic systms can be bridged by (CH 2 ) n chains of any desired length. In addition, (CH 2 ) chains can be split off together with two SO 2 molecules, with recombination of the remaining centers, resulting in ring contraction by four to n atoms. However, sulfone pyrolysis is of importance not only as a ring‐contraction method but as a crucial final step in the synthesis of multi‐membered hydrocarbon cycles, e.g. of the phane type.