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Photochemische Umwandlungen, 41 [1] 3ω → 3 π‐Isomerisierungen von Monohetero‐trishomobenzol‐derivaten. Vorläufige mitteilung
Author(s) -
Prinzbach H.,
Stusche D.
Publication year - 1971
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19710540234
Subject(s) - chemistry , isomerization , medicinal chemistry , stereochemistry , organic chemistry , catalysis
The all‐ cis ‐oxa‐ and azatrishomobenzene diesters 4a and 4b resp. undergo thermally a very clean 3ω → 3π isomerization reaction yielding the heterocyclonona‐2, 5, 8‐triene derivatives 6a and 6b resp. ( E a = 27.4 and 26.5 kcal/mole). In contrast, the cis , cis , trans ‐oxatrishomobenzene diester 9 is stable up to 170°. Some applications and limitations of this 3ω → 3π‐route to iso‐ and heterocyclononatriene derivatives are discussed.