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Cycloaddition von benzothiet an oxime, oximether und oximester
Author(s) -
Meier Herbert,
Saul Klaus,
Mengel Rudolf,
Niedermann HansPeter
Publication year - 1991
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570280402
Subject(s) - cycloaddition , chemistry , oxime , stereospecificity , ring (chemistry) , adduct , thiazine , medicinal chemistry , stereochemistry , organic chemistry , catalysis
Benzothiete 1 generates by thermal ring opening an 8π electron system 2 which undergoes [8π + 2π] cycloaddition reactions with the oxime systems 3a‐g . In accordance with the FMO theory the 1,3‐thiazine derivatives 4a‐g are formed in a regiospecific and 4f additionally in a stereospecific manner. The O ‐acylated adducts 4h‐j enter the same cycloaddition; however, an elimination reaction 4 ← 5, 6 can provoke the addition of a second benzothiete, yielding the tetracyclic compounds 7j , and 8i,j .