Talk:Molozonide

Once the intermediate molozonide forms don't the two carbons that were in an sp2 hybridized orbital take on an sp3 hybridized formation? The carbon molecule and the substituents attached to it are no longer planar (as noted by the dashed line). Also, the bond angle is much closer to being tetrahydral than a 120degree angle. --jorgekluney

This is no longer considered the molozonide. There has been some discussion about this intermediate in the literature and is considered the primary ozonide now (although some text books still consider it as the molozonide). In the early years of the ozonolysis, Staudinger proposed a four member ring addition of ozone to the alkene and created the term molozonide. Subsequent research on the mechanism (primarily by Criegee) of ozonolysis showed that the four member ring was incorrect. Later Bailey began to call the 1,2,3-trioxolane a primary ozonide in order to distinguish it from the Staudinger molozonide. I have seen the IUPAC reference and I am at a loss as to why it is still called the molozonide. This should be changed. As to the question above, the two carbons do rehybridize to sp3. In the cycloreversion, the carbons rehybridize again to sp2 to form the carbonyl oxide and carbonyl intermediates. Weitu (talk) 17:01, 3 September 2009 (UTC)Weitu