Allene oxide-cyclopropanone systems

Recently, Chan showed that the allene oxide-cyclopropanone system can be formed starting with the silylated epoxide (16). Fluoride ion promoted elimination was carried out... 

Allene oxide-cyclopropanone systems. Treatment of the oxide of 3-chloro-2-triphenylsilyl-l-phenylpropene (1) leads to 3-elimination of (Ce H5 >3 SiF and... 

Allene oxide-cyclopropanone systems, 482 Allenes, 95, 143-144, 223, 523, 619 Allenic alcohols, 147-148, 269, 325 AUenic esters, 635... 

Cyclopropanones are involved in the Favorski rearrangement, and there has been considerable interest in the allene oxide-cyclopropanone system. Estimation of the relative energies of the various structures involved (Scheme 62) is notoriously... 

Another possible route to cyclopropanones is via the isomerism of allene oxides, i.e., 60 61. While valence isomerism has been established in related systems such as 62 63 54>, only two cyclopropanones have as yet been prepared by this method and its usefulness appears limited. 

An interesting route to the cyclopropanone system involves the rearrangement of allene oxides, usually generated by the epoxidation of allenes. Thus, 1,3-di-t-butylallene oxide (11) may be prepared by the reaction of 1,3-di-t-butylallene with m-chloroperbenzoic acid. Heating 11 to 100 °C leads to isomerization, forming truns-2,3-di-t-butylcyclopropanone (10) (Scheme 4) Similarly, 1,1-di-t-butylallene (15) yields 2,2-di-t-butylcyclopropanone with peracetic acid (equation 7) ... 

---

See also in sourсe #XX -- [ ]

---