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Synthesis and Cycloadditions of Monomeric Selenobenzophenone
Author(s) -
Erker Gerhard,
Hock Regina,
Krüger Carl,
Werner Stefan,
Klärner FrankGerrit,
ArtschwagerPerl Uwe
Publication year - 1990
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.199010671
Subject(s) - monomer , chemistry , diene , solid state , hexa , product (mathematics) , high pressure , medicinal chemistry , polymer chemistry , stereochemistry , organic chemistry , polymer , thermodynamics , physics , natural rubber , geometry , mathematics
Selenobenzophenone (1), prepared from Ph 2 C PPh 3 and Se, is monomeric in solution and dimeric in the solid state . Cycloadditions of dienes to 1 proceed at room temperature under normal pressure as multistep reactions, as shown by the exclusive formation of cis ‐ 2 from both trans, trans‐ and cis, trans ‐hexa‐2,4‐diene. When the pressure is raised to about 12 kbar, cis, trans ‐hexadiene affords 60% of trans ‐ 2 , the product of the concerted hetero‐Diels–Alder reaction.