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Synthesen und Thermolysen von 1-Alkinyl-2-methyl-1,2-epoxy-cycloalkanen. - Versuche zur Ringerweiterung um drei Kohlenstoffatome by Martin Karpf; André S. Dreiding is a Chemistry article available to read on EtoBox.
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**Syntheses and Thermolyses of 1‐Alkynyl‐2‐methyl‐1,2‐epoxy‐cycloalkanes. ‐ Attempts at Ring Enlargement by Three Carbon Atoms** The 1‐alkynyl‐2‐methyl‐1,2‐epoxy‐alkene **2** and ‐cycloalkenes **9, 28** and **29** were obtained by epoxidation of the conjugated en‐ynes **1, 7, 26** and **27**. The 12‐membered ring en‐ynes **26** and **27** were synthesized by ethynylation or propynylation of 2‐methylcyclododecanone (**19**) to the 1‐ethynyl‐ or 1‐(1′‐propynyl)‐cyclododecanols **20 A/B** and **21 A/B**, respectively, followed by dehydration to give separable mixtures of the regio‐ and stereoisomeric en‐ynes **22, 24, 26** and **23, 25, 27**, respectively. Gas‐phase thermolyses of the epoxides **2, 9, 28** and **29** were carried out under reduced pressure through a quartz tube at 550–600°. The formation of 5‐hexine‐2‐one (**3**) and 4,5‐hexadien‐2‐one (**4**) from **2** can be explained by [1, 5]‐ and [1, 3]‐ hydrogen shifts, respectively, and subsequent __Claisen__‐type rearrangements. Thermolysis of the six‐membered carbocyclic epoxide **9** induced the expected ring expansion by three carbon atoms to give 14% 4‐cyclononynone (**12**), along with the ketones **13, 14** and **15** a
Who reads Synthesen und Thermolysen von 1-Alkinyl-2-methyl-1,2-epoxy-cycloalkanen. - Versuche zur Ringerweiterung um drei Kohlenstoffatome?
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- Author
- Martin Karpf; André S. Dreiding
- Publisher
- John Wiley and Sons; Wiley (John Wiley & Sons); Wiley-Blackwell; Wiley (ISSN 0018-019X)
- Published
- 1977
- Language
- DE
- Field
- Chemistry (Physical Sciences)