Thermische Umlagerung von 2‐Oxa‐bicyclo [3.3.1]‐non‐7‐en‐3‐on; eine neuartige Lactonumlagerung. Vorläufige Mitteilung | Zendy

Fráter György | Zendy

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Thermische Umlagerung von 2‐Oxa‐bicyclo [3.3.1]‐non‐7‐en‐3‐on; eine neuartige Lactonumlagerung. Vorläufige Mitteilung

Author(s) -

Fráter György

Publication year - 1979

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.19790620231

Subject(s) - chemistry , sigmatropic reaction , yield (engineering) , bicyclic molecule , lactone , alkylation , boiling , medicinal chemistry , stereochemistry , organic chemistry , thermodynamics , catalysis , physics

Thermal Rearrangement of 2‐Oxa‐bicyclo [3.3.1]‐non‐7‐en‐3‐ones; a Novel Lactone Rearrangement Lactone (+)‐ 2 was prepared by iodolactonisation and subsequent elimination in 51% yield from the known acid (+)‐ 1 ( Scheme 1 ). Alkylation of (+)‐ 2 furnished (+)‐ 3a , (+)‐ 3b and (+)‐ 3c , respectively ( Scheme 2 ). Heating of (+)‐ 3a in boiling DMF racemized the compound ((+)‐ 3a ⇆ (−)‐ 4a ). Heating of (+)‐ 3b and (+)‐ 3c , respectively, equilibrated them with (−)‐ 4b and (−)‐ 4c , respectively. This results are interpreted as a [3.3]‐sigmatropic rearrangement with a transition state as depicted in a .

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