I have a weak spot for new, SIMPLE and potentially powerful transformations.

I am certainly not alone, and I am certainly not the first to confess to this preference. Some call it Occam’s razor, others the KISS principle (Keep it simple, stupid). The origin is tracable even to Aristotle (who lived some 3-400 years before Jesus H. Christ), who apparently said Pluralitas non est ponenda sine necessitate (“Plurality is not to be posited without necessity”). What beats me is why an ancient Greek philosopher would speak Latin…

Err… Back to chemistry.

Here is, in my humble opinion, a really classy example of what I mean. Take a benzylic ether. One equivalent NBS gives the aldehyde; two equivalents for the ester.

Awesome transformation

JOC 2010, 75, 3507-3510. (Available here.)

We can talk about the need for light. Just as a radical initiator? Would AIBN do the trick? Or does the light do something even more exciting (pun intended)?

 

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