This Cursed Molecule Will Teach You About Aromaticity | Pagodane & dodecahedrane synthesis chemistry
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- Опубліковано 10 чер 2024
- 🧠 The chemists who discovered pagodane described it simply but accurately: this is a highly complex, aesthetically appealing molecule. In this video, you will see how Prinzbach and co-workers used quite straight-forward chemical reactions to synthesize the impressive pagodane, leveraging symmetry and inherent reactivity. Also, we will learn how it's connected to the isomer dodecahedrane and the unique case of sigma-bishomoaromaticity present in one of its derivatives.
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00:00 Pagodane and chemical synthesis of complex frameworks & natural products
01:04 Context on pagodane's synthesis: Aldrin and isodrin, potent insecticides
02:08 Prinzbach's forward synthesis of pagodane
05:16 Dodecahedrane synthesis from pagodane
07:11 Sigma-homobisaromaticity of a cyclobutanoid system in pagodane
References:
- "Pagodane": the efficient synthesis of a novel, versatile molecular framework: J. Am. Chem. Soc. 1987, 109, 15, 4626
- Stable carbocations. Part 267. Pagodane dication, a unique 2.pi.-aromatic cyclobutanoid system: J. Am. Chem. Soc. 1986, 108, 4, 836
- From an Insecticide to Plato's Universe-The Pagodane Route to Dodecahedranes: New Pathways and New Perspectives: Angew. Chem. Int. Ed. Engl. 1994, 33, 2239
- Dodecahedrane: J. Am. Chem. Soc. 1982, 104, 16, 4503
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Some recommended books on organic synthesis:
- Clayden, Greeves, Warren; Organic Chemistry (basic organic chemistry knowledge)
- Wyatt, Warren; Organic Synthesis: The Disconnection Approach (excellent introduction to retrosynthesis)
- Kurti, Czako; Strategic Applications of Named Reactions in Organic Synthesis (extensive toolkit of functional group reactions and applications thereof with common conditions)
- Nicolaou; Classics in Total Synthesis 1-3 (the ultimate total synthesis trilogy)
- Nicolaou; Molecules That Changed the World (the world's most important molecules and their impact on everyday life)
- Carreira, Kvaerno; Classics in Stereoselective Synthesis (compilation of the groundbreaking methods of stereoselective synthesis and application to synthesis of stereochemically complex structures) - Наука та технологія
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Someone should do total synthesis of this starting only with carbon and hydrogen.
Yea fuggen gday cants. Today were ganna make some Dodecahedrane using the lump of coal Scott Morrison brought into parliament, and some benzine I found in me nans gin cabinet.
Shit, this script rights it’s self and it’s fkn gold!!!!!!
I can’t find a better word to describe this synthesis than “symphonic”. It combines so many different yet basic reactions in masterful harmony.
Spot on!
The old-fashioned synthesis of Pagodane is so fascinating in its simplicity! It is always exciting to see how authors are able to create something outstanding utilizing almost trivial transformations.
Facts. Using symmetry is also powerful!
Have just covered most of the reactions used in this total synthesis in my uni course right now. Its amazing to see how powerful pericyclic chemistry is and some of its applied uses. Love the videos
Nice! You are right, pericyclics are insanely useful, especially also for tertiary or quaternary centers
Let me know any thoughts on this video and any suggested topics in general - what would you like to see more of?
❓basic chemistry stuff or advanced?
❓natural products, pharmaceuticals, random nice looking molecules or materials?
❓total synthesis, medicinal chemistry or reaction methodologies?
Hey man, your videos are absolutely amazing!!!! Please upload a video per day where you just read crazy papers like this. Screw the animations, break the stick and balls out. Everyone loves balls ❤
Keep up the good work! 😊
I want total synthsis involving organic chemistry!
@@kshitijkumar5629 Next video will be focused on this! But quite advanced
@@totalsynthesis hey, can you check that MDMA video comment section, i asked some doubts regarding the reactions.
@@kshitijkumar5629 ive just replied
Wow, what a brilliant story! Thank you for putting in all the effort, it was totally worth it!
🙏
An odd carbon structure that would be an interesting total synthesis is iceane. It is the building structure for the mineral lonsdalite in the same way that adamantane is for diamond. The mineral is only found in space and has a theoretical moh’s hardness higher than diamond due to its hexagonal diamond lattice compared to the typical cubic diamond lattice. There wasn’t much literature I could find on it however there is a few synthesis papers.
Nice, seems underrated af
Love your videos, so thankful there is at least a little bit of orgo/synth chem content of this style.
Thanks man!
This synthesis is so satistying
Nice!
I know is "normal" in organic synthesis but ring contractions still fascinate me. The electrons of the carbons in the ring jump!
Oh yeah. Stuff like regioselective migrations as seen in Baeyer-Villiger reactions and others are really nice
Keep griding friend 😤😤😤
💪🔥🔥
Now make super dodecahedrane just like super benzene.
Can it be somehow nitro-oxydated or manganase oxy-dated to be explosive?
🤣 yeah after closure to pagodane, you might nitrate using the ester groups instead of decarboxylating
@@totalsynthesis Is it strong explosive?
@@_juraj_ Without nitros not at all, with nitros maybe but probably nothing crazy
Yummy