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THIS is heterocyclic chemistry

By drfreddy On May 28th, 2012 · 5 Comments

A cascade, fifteen or so step, one-pot reaction yielding one freak heterocycle as the main product, with more sulfurs in it than … I dunno what.

Angew. Chem. Int. Ed. 1997, 36, 281-283. (DOI: 10.1002/anie.199702811)

Listen to this. Hünig’s base acts as a reactant and electrophilic sulfurs play the main characters. I […]

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C-F bond breakage

By drfreddy On May 22nd, 2012 · 7 Comments

Frequent readers know I have voiced my concern about fluorinated organic compounds, especially those containing aliphatic fluorides, from time to time. New fluorination recipes pop up all of the time, and more and more pharmaceuticals contain one or several very stable C-F bonds, which may or may not spell trouble for future generations. In the […]

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The stupidest abbreviation in chemistry

By drfreddy On May 20th, 2012 · 11 Comments

Of all the widely accepted ones out there, according to you, which is it? I vote for the free radical scavenger they put in ethers to avoid peroxide disasters

BHT – Butylated HydroxyToulene

It is preposterous. Because:

1. ‘Butylated’ implies butyl groups were added to a core structure (synthetically), which is not the case

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Name A and B!

By drfreddy On May 17th, 2012 · 7 Comments

Here is a one-step transformation that I think few, perhaps not even Corey,* would come up with upon a traditional retrosynthetic analysis.

A and B are everyday organic reagents. The solvent is DCM and the temperature is around 0 °C. No metals, complexes or weird oxidation level crap. So – go ahead and name […]

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My new friend

By drfreddy On May 8th, 2012 · Leave a Comment

I have a new BFF. Meet this mother of an ate-complex:

Recipe inhere: J. Org. Chem. 2007, 72, 5113-5118. (DOI: 10.1021/jo070643y)
The structure looks scary, but its preparation is quite straightforward, actually.

My new friend was able to ortho-lithiate an ‘impossible’ starting material and allowed me to introduce an electophile in […]

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