The New Clayden pp. 825 – 851

I’m reading a lot of math (about which much more in a future post).  It shifts slightly they way I’m reading Clayden.  In math you want to be certain that you understand exactly what you’re reading.  In this chapter particularly, the understanding is the easy part.  I don’t see how anyone with any spatial sense can find stereo electronics hard.  It seems that the explanations are longer and more detailed than they need to be.  Nonetheless the chapter is filled with clever syntheses, none of which appear to use the disconnection approach.

p. 828 — Nice to see something that isn’t known for sure in an introductory textbook (why small nucleophiles PREFER an axial attack). 

p. 833 — Cyclohexane is slightly bent.  How slightly? 

p. 837 — The transition state is the same for both reactions (formation and destruction of an epoxide of an alkene).  Shouldn’t it be said that this true for all reactions?  Or am I wrong?

p. 844 — Formation of the tricyclo (0, 2, 3) system is incredibly clever.

p. 846 — The reactions forming all sorts of extra rings in the cis decalins are very clever, although you need to think about them occuring in space, probably the original thought about them occurred by drawing the rings flat and seeing what would happen when anions would form and what they would attack.  Although clever, these reactions really don’t result from new concepts, just applying them to molecules in space.  Ditto for endo/exo reactions.  One of the attractions of organic chemistry, there really aren’t a high number of different concepts, but the cleverness arises in applying them.  It’s why I find organic far easier than math which will be the subject of a future post. 

p. 848 – 9 — The beautiful synthesis of the C and D rings of the steroid nucleus with the appropriate stereochemistry.  One can regard a synthesis like this as a mathematical proof of a theorem, with the theorem the final product and the steps of the proof, the steps of the synthesis.  

Chapter End — Intriguing how clever it all is, and how little the disconnection approach to synthesis had to say about any of the syntheses.  Clearly they both have their roles. 
 
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