Cleavage of Zero Bridged Single Bonds in Bicycles

VIII/91 — VIII/92 — VIII/93 — VIII/90 is like a chemical perpetuum mobile (perpetual motion). However, after one sequence the amount of VIII/90 is reduced to approximately 40 %  

Further examples are the synthesis of 5-cyclodecynone [52][53] and the fragmentation of l,2-epoxy-3-diazirine-5a-androstan-17/ -ol by treatment with sodium iodide and acetic acid. (The A ring is opened between C(2) and C(3) to give the l-oxo-2,3-alkyne derivative) [54], 

Cleavage of Zero Bridged Single Bonds in Bicycles 

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VIII.2. Cleavage of Zero Bridged Single Bonds in Bicycles... 

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