Iridium‐Catalyzed β‐Alkynylation of Aliphatic Oximes as Masked Carbonyl Compounds and Alcohols

An Ir‐catalyzed C(sp3)βˆ’H alkynylation of aliphatic ketones, aldehydes, and alcohols was achieved by using the corresponding oxime derivatives and a IrIII catalyst. This general reaction is selective towards primary C(sp3)βˆ’H bonds and can be used for the late‐stage Cβˆ’H alkynylation of complex molecules.

Abstract

An Ir‐catalyzed C(sp3)βˆ’H alkynylation of aliphatic ketones, aldehydes, and alcohols was achieved by using the corresponding oxime derivatives and a IrIII catalyst. This general reaction is selective towards primary C(sp3)βˆ’H bonds and can be used for the late‐stage Cβˆ’H alkynylation of complex molecules.

https://ift.tt/2U98Kam

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πŸ‘€︎ u/TomisMeMyselfandI
πŸ“…︎ Apr 15 2020
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Why are cyclic molecules so prevalent in chemistry?

When observing all the different types of organic molecules that exist, many seem to contain ring structures and are almost iconic in chemistry. Particularly in biological systems, many drugs (both naturally derived and synthetic) and biological molecules (sugars ect) seem to contain some sort of cyclic ring(s).

Why are rings so common? Is it because these type of structures are inherently stable? I know aromaticity leads to an increase in stability, but what about aliphatic compounds?

Note: I am a physical chemistry PhD student, but this has recently come to mind. Cheers!

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πŸ‘€︎ u/Borris-N-Friends
πŸ“…︎ Dec 21 2021
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Dragendorff stain not staining specific amines

So the Dragendorff stain has been amazing for detecting aliphatic secondary and tertiary amines, but one compound I make has 3 secondary amines and one tertiary amines and I can't get it to stain. Every other related compound I've made stains beautifully and fast. Has anyone seen that some amines just won't stain with Dragendorff? Any other potential stains for a molecule that only has secondary amines and one tertiary amine and an amide on it?

Edit for reference this is the version of the stain I made to use https://www.silicycle.com/faq/thin-layer-chromatography/stains-for-tlc-plates I've also remade the stain before with no change

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πŸ‘€︎ u/Ru-tris-bpy
πŸ“…︎ Dec 05 2021
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Bedliner

I’m building my maverick at the dealer tomorrow and I’m wondering if I should add a bedliner. Do most of the videos showing a maverick have one included?

Did you include one in your build?

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πŸ‘€︎ u/patsox799
πŸ“…︎ Jun 28 2021
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So TIL that my world could feasibly invent plastics before their bronze age. This is canon now.

>I'm keeping the original post in tact, but be sure to check the edits! Some changes are being made...
>
>Also! Thank you so much for the silver et al, and for all the great advise! A lot of people are explaining that we had plastics in antiquity if you consider anything malleable ("plastic") or anything with polymers to be plastic. Thanks for the learning opportunity! But to be clear, I intended to mean oil-based plastic, like (in this case) polyethylene: what our plastic bags and containers and all are made of.
>
>Thank you all for your help thus far. This has been thrilling for me through and through, and a great learning experience for someone who only ever took a chemistry class in high school (and got, like, a high C, I think).

So, any critique from somebody more knowledgeable about chemistry and plastics would be appreciated.

First off though, a little background about my planet, Nulaxia (name pending):

  • It's a cold planet orbiting an L-class "star"; its temperatures are about -100 Β°C on average.
  • It has 3-4x the atmospheric pressure of Earth's.
  • Like Titan, it is a hydrocarbon world. In Nulaxia's case, its oceans contain ethane and other organics (in liquid form) instead of water, and its atmosphere contains methane (in gas form) instead of oxygen. (EDIT: To be clear, the atmosphere is still mostly nitrogen!)
  • Fire can still burn on this planet, using the methane in the air as fuel, and the "burning material" as oxidizer. For example, you can burn saltpeter similar to how you could burn wood on Earth. (No, striking a match won't burn up the entire planet; you need an oxidizing agent!) So, heating / cooking / smelting is possible.

So yeah, it may seem obvious that they can make plenty of plastic on a planet with oil for oceans, right? But...before the bronze age?

Hear me out.

  • A decent percentage of the ocean's composition is C2H4.
  • C2H4 can be separated from the other hydrocarbons in the oceanic mix through evaporation.
  • Contaminants can be burned off through melting.
  • At 160 Β°C, C2H4 ("ethylene") polymerizes.

And what does that form? Only one of the most common plastics on Earth.

For context, copper may be forged at 900 Β°C, and bronze is smelted at a similar 913 Β°C. Silicate sand melts into glass at 1700 Β°C. Plastic would be easier to make than metal!

If all they have to do is separate a liquid from their "water" the way we might separate wate

... keep reading on reddit ➑

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πŸ‘€︎ u/KupferudelWolf
πŸ“…︎ Aug 03 2021
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SERIOUS: This subreddit needs to understand what a "dad joke" really means.

I don't want to step on anybody's toes here, but the amount of non-dad jokes here in this subreddit really annoys me. First of all, dad jokes CAN be NSFW, it clearly says so in the sub rules. Secondly, it doesn't automatically make it a dad joke if it's from a conversation between you and your child. Most importantly, the jokes that your CHILDREN tell YOU are not dad jokes. The point of a dad joke is that it's so cheesy only a dad who's trying to be funny would make such a joke. That's it. They are stupid plays on words, lame puns and so on. There has to be a clever pun or wordplay for it to be considered a dad joke.

Again, to all the fellow dads, I apologise if I'm sounding too harsh. But I just needed to get it off my chest.

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πŸ‘€︎ u/anywhereiroa
πŸ“…︎ Jan 15 2022
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Blind Girl Here. Give Me Your Best Blind Jokes!

Do your worst!

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πŸ‘€︎ u/Leckzsluthor
πŸ“…︎ Jan 02 2022
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This subreddit is 10 years old now.

I'm surprised it hasn't decade.

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πŸ‘€︎ u/frexyincdude
πŸ“…︎ Jan 14 2022
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Dropped my best ever dad joke & no one was around to hear it

For context I'm a Refuse Driver (Garbage man) & today I was on food waste. After I'd tipped I was checking the wagon for any defects when I spotted a lone pea balanced on the lifts.

I said "hey look, an escaPEA"

No one near me but it didn't half make me laugh for a good hour or so!

Edit: I can't believe how much this has blown up. Thank you everyone I've had a blast reading through the replies πŸ˜‚

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πŸ‘€︎ u/Vegetable-Acadia
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What starts with a W and ends with a T

It really does, I swear!

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πŸ‘€︎ u/PsychedeIic_Sheep
πŸ“…︎ Jan 13 2022
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What is a a bisexual person doing when they’re not dating anybody?

They’re on standbi

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πŸ‘€︎ u/Toby-the-Cactus
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Geddit? No? Only me?
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πŸ‘€︎ u/shampy311
πŸ“…︎ Dec 28 2021
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Why did Karen press Ctrl+Shift+Delete?

Because she wanted to see the task manager.

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πŸ‘€︎ u/Eoussama
πŸ“…︎ Jan 17 2022
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Some facts

For last minute revision. Add more in the comments if you want to contribute

CHEMISTRY

  • KMnOβ‚„ in acidic medium is a stronger oxidizing agent than KMnOβ‚„ in a basic medium

  • Aqueous KOH favours Substitution, Alcoholic KOH favours Elimination

  • Higher temperatures favour Elimination

  • Hydroboration-Oxidation: Anti-Markovnikov addition of water

  • OxyMercuration-DeMercuration: Markovnikov addition of water (NO Carbocation rearrangements in both)

  • Acid catalysed hydration(H+/Hβ‚‚0): carbocation rearrangements CAN occur, pay attention

  • LiAlHβ‚„: Very strong reducing agent

  • NaBHβ‚„: Slightly weaker, but still a good reducing agent

  • DIBAL-H: Weaker reducing agent than LiAlHβ‚„

  • Reduction of carbonyl compounds gives alcohols

  • Reduction of Ketones gives secondary alcohol

  • Reduction of Aldehydes gives primary alcohol

  • Reduction of nitrogen derivatives gives amines

  • Decarboxylation of simple carboxylic acids requires very high temperatures and the compounds may decompose, but the beta-keto carboxylic acids give COβ‚‚ even on mild heating

  • Ozonolysis can be used to convert alkenes to aldehydes and ketones

  • Kβ‚‚Crβ‚‚O₇ cannot oxidize ketones

  • hot alkaline KMnOβ‚„ converts primary alcohols straight to acids

  • hot alkaline KMnOβ‚„ converts alkenes to ketones or acids

  • cold alkaline KMnOβ‚„ converts alkenes to vicinal glycols (syn addition)

  • CrO₃ in dil.Hβ‚‚SOβ‚„ (Hβ‚‚CrOβ‚„) : Jones' reagent (Weak Oxidizing agent)

  • cold, dilute, alkaline KMnOβ‚„: Baeyer's reagent (Strong Oxidizing agent)

  • Zn+conc.HCl (ZnClβ‚‚): Lucas' reagent (used in Lucas' test)

  • Hβ‚‚/Pd/BaSOβ‚„: Lindlar's catalyst (reduces alkynes to cis-alkenes)

  • Na/Li + liq. NH₃ : reduces alkynes to trans-alkenes

  • Pyridinium Chlorochromate (PCC): converts primary alcohol to aldehyde

  • Collin's reagent (Pyridine with CrO₃ in dichloromethane): primary alcohol to aldehyde

  • THF (Tetrahydrofuran): often used with BH₃

  • m-CPBA (metaChloroBenzoic Acid): used in epoxidation

  • Hinsberg reagent: Benzene Sulfonyl Chloride (Ph-SOβ‚‚Cl)

  • Tollen's test: +ve for aliphatic/aromatic aldehydes, alpha-hydroxy ketones, aldehydes and amines, formic acid

  • ! Tollen's test =/= Silver mirror test ! eg.Acetylene only gives Tollen's test but not Silver mirror

  • Fehling's test: +ve for reducing sugars (red-brown ppt), aliphatic aldehydes, alpha-hydroxy ketones, aldehydes and amines

  • Lucas' test: to distinguish prim/sec/tert alcohols

  • Carbylamine test: test for primary amines

  • Hinsberg test: distinguish between prim/sec/tert

... keep reading on reddit ➑

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πŸ‘€︎ u/elktron
πŸ“…︎ Jul 21 2021
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I wanna hear your best airplane puns.

Pilot on me!!

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πŸ‘€︎ u/Paulie_Felice
πŸ“…︎ Jan 07 2022
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E or ß?
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πŸ‘€︎ u/Amazekam
πŸ“…︎ Jan 03 2022
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What did Spartacus say when the lion ate his wife?

Nothing, he was gladiator.

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πŸ‘€︎ u/rj104
πŸ“…︎ Jan 15 2022
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Pun intended.
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πŸ‘€︎ u/Sharmaji1301
πŸ“…︎ Jan 15 2022
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No spoilers
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πŸ‘€︎ u/Onfour
πŸ“…︎ Jan 06 2022
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Covid problems
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πŸ‘€︎ u/theincrediblebou
πŸ“…︎ Jan 12 2022
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These aren't dad jokes...

Dad jokes are supposed to be jokes you can tell a kid and they will understand it and find it funny.

This sub is mostly just NSFW puns now.

If it needs a NSFW tag it's not a dad joke. There should just be a NSFW puns subreddit for that.

Edit* I'm not replying any longer and turning off notifications but to all those that say "no one cares", there sure are a lot of you arguing about it. Maybe I'm wrong but you people don't need to be rude about it. If you really don't care, don't comment.

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πŸ‘€︎ u/Lance986
πŸ“…︎ Dec 15 2021
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I had a vasectomy because I didn’t want any kids.

When I got home, they were still there.

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πŸ‘€︎ u/demotrek
πŸ“…︎ Jan 13 2022
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What did 0 say to 8 ?

What did 0 say to 8 ?

" Nice Belt "

So What did 3 say to 8 ?

" Hey, you two stop making out "

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πŸ‘€︎ u/designjeevan
πŸ“…︎ Jan 03 2022
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Spi__
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πŸ‘€︎ u/Fast_Echidna_8520
πŸ“…︎ Jan 11 2022
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I dislike karma whores who make posts that imply it's their cake day, simply for upvotes.

I won't be doing that today!

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πŸ‘€︎ u/djcarves
πŸ“…︎ Dec 27 2021
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The Ancient Romans II
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πŸ‘€︎ u/mordrathe
πŸ“…︎ Dec 29 2021
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I'd like to dedicate this joke to my wisdom teeth.

[Removed]

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πŸ‘€︎ u/ThoughtPumP
πŸ“…︎ Jan 14 2022
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Where do you find a cow with no legs?

Where ever you left it πŸ€·β€β™€οΈπŸ€­

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πŸ‘€︎ u/kitkatty0309
πŸ“…︎ Jan 16 2022
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I did it, I finally did it. After 4 years and 92 days I went from being a father, to a dad.

This morning, my 4 year old daughter.

Daughter: I'm hungry

Me: nerves building, smile widening

Me: Hi hungry, I'm dad.

She had no idea what was going on but I finally did it.

Thank you all for listening.

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πŸ‘€︎ u/Sk2ec
πŸ“…︎ Jan 01 2022
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It this sub dead?

There hasn't been a post all year!

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πŸ‘€︎ u/TheTreelo
πŸ“…︎ Jan 01 2022
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How do you stop Canadian bacon from curling in your frying pan?

You take away their little brooms

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πŸ‘€︎ u/Majorpain2006
πŸ“…︎ Jan 09 2022
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School Was Clothed
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πŸ‘€︎ u/Kennydoe
πŸ“…︎ Jan 08 2022
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Remember that joke I told you about the chiropractor?

It was about a weak back.

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πŸ‘€︎ u/tanglwyst
πŸ“…︎ Jan 16 2022
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Naan-negotiable
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πŸ‘€︎ u/sjmaeff
πŸ“…︎ Jan 16 2022
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Letting loose with these puns
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πŸ“…︎ Jan 13 2022
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Couch potato
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πŸ“…︎ Dec 31 2021
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Baka!
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πŸ‘€︎ u/ridi86
πŸ“…︎ Jan 09 2022
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All dad jokes are bad and here’s why

Why

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πŸ‘€︎ u/LordCinko
πŸ“…︎ Jan 13 2022
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