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Subject: Re: [DCHAS-L] Safer Diels-Alder reaction

Date: Jul 19, 2019 15:59 UTC

Author: Andrew Garrett <garretta2**At_Symbol_Here**BEREA.EDU>

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Subject: Re: [DCHAS-L] Safer Diels-Alder reaction

Date: Jul 19, 2019 16:15 UTC

Author: Harry Elston <harry**At_Symbol_Here**MIDWESTCHEMSAFETY.COM>

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From: Rob Toreki <info**At_Symbol_Here**ILPI.COM>

Subject: Re: [DCHAS-L] Safer Diels-Alder reaction

Date: Jul 19, 2019 16:00 UTC

Reply-To: ACS Division of Chemical Health and Safety

In-Reply-To: [DCHAS-L] Safer Diels-Alder reaction

Demystify: 

A quick web search on green Diels Alder reveals these:

http:​//homepage.smc.edu/KLINE_PEGGY/Organic/Lab_Reports_Ch_24/Diels_Alder_Student_HO.pdf

https://pubs.acs.org/doi/abs/10.1021/ed086p488 (access required, but your ACS membership gives you 25 free articles a year if you don't have institutional access).

https://pubs.rsc.org/en/content/articlelanding/2009/gc/b813485e#!divAbstract

That said, if this is a majors course rather than general organic, I am old school enough to believe we need to teach students how to handle materials like dicylopentadiene. The Cp ligand is a bedrock staple of organometallic chemistry and is usually derived from the cracking of dicyclopentadiene followed by deprotonation of the CpH.

Rob Toreki


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On Jul 19, 2019, at 10:40 AM, Denlinger, Kendra <denlingerk**At_Symbol_Here**XAVIER.EDU> wrote:

Hello everyone,
I'm teaching an organic lab right now (my first time teaching this course), and we're supposed to do a Diels-Alder reaction in a few weeks. It's a reaction between cyclopentadiene and maleic anhydride, and the students are supposed to "crack" dicyclopentadiene to cyclopentadiene using a distillation with mineral oil, and then react cyclopentadiene with maleic anhydride in ethyl acetate (which is a very exothermic reaction). Long story short, the whole thing sounds like an accident waiting to happen. 

I know there has got to be a safer (and maybe even greener!) Diels-Alder reaction out there for organic lab students, but I don't know exactly where to look and thought maybe it would be a good question for all of you! I don't have a long time to search and test things, so if someone has a Diels-Alder procedure you use at your university that works and is safer, I would love to hear about it!

Thanks for any assistance!
Kendra Denlinger