Tosyl Puns

I don't know how blanket bans would deal with those over the world, but I suppose that there is a great potential for them to be pro drugs of known chems.

There are some drawbacks, however. It would require the drug to be taken orally, and it may need a lot of time for the drug to be fully converted, thus resulting in something that would be similar to a Vyvanse-like version of the substance.

For N-t-BOC-MDMA, for example:

"The possibility that the t-BOC-MDMA may act as a pro-drug following ingestion was explored by exposure to simulated gastric juice (pH 1.5) and monitored by NMR (37° C) at various intervals. The majority of t-BOC-MDMA was converted to MDMA after 305 min,..."

source: https://doi.org/10.1002/dta.2059

Indeed, this sucks. There would be no use for such pharmacodynamics for MDMA. But anyway, it's Very likely that this molecule would be scheduled in most, if not all, legislations around the world. It was just an example that was formally tested about the potential for it to be a pro-drug.

The t-BOC and p-tosyl versions of methamphetamine were already seized by thie-... I mean, law enforcement agencies out there, and 500 Kg of t-BOC-ketamine (RIP) had the same unfortunate fate once, in Taiwan.

Seems like it's already a thing and the RC market may have some use to it.

If the drugs keep the same conversion profile of t-BOC-MDMA to MDMA, I suppose that only the pro drugs of functional stimulants, and maybe arylcyclohexylamines, could be useful.

However, the same paper quoted before reported a high yield conversion in aqueous HCl, at 80°C, in only 30 minutes.

Any opinions? I would certainly give it a try.

So, I know of the sulfonation of toluene as a route to pTsOH, however, I am wondering if there's a way to get pTsOH from TsCl?

The direct copolymerization of epoxides with p‐tosyl isocyanate was achieved in the presence of trialkylborane and polyurethanes could be obtained without the formation of cyclic isocyanurate, in high linear/cyclic and urethane/imidocarbonate selectivity. The reported method provides access to the modification of properties of other polymers, especially aliphatic polycarbonates generated under the same conditions.

Abstract

The direct copolymerization of p‐tosyl isocyanate (TSI) with epoxides, initiated by onium salts in the presence of trialkylborane, to produce polyurethanes is reported. The rate of copolymerization and the (regio)selectivity were investigated in relation to the trialkylborane and the initiator used. Under optimized conditions such copolymerizations have been successfully performed for a wide range of epoxides, including ethylene oxide, propylene oxide, 1‐octene oxide, cyclohexene oxide, and allyl glycidyl ether. These copolymerizations afford a new category of polyurethanes, clear of side products such as cyclic oxazolidinone, isocyanurate, and poly(isocyanate) linkages. The experimental conditions used in this work are compatible with those for the organocatalytic (co)polymerization of other oxygenated monomers and CO2, holding the potential for their terpolymerization with p‐tosyl isocyanate and the development of new materials with unprecedented properties.

https://ift.tt/35AGaV9

So I read that mesylation/tosylation can make alcohol a better leaving group in SN reactions. I also saw that mesylation/tosylation can act as protecting groups to prevent the alcohols from reacting. Both make sense to me, but now after some thought this effect seems kind of "contradictory", in that it's making the -OH both more and less reactive. Does anyone mind explaining how mesylation/tosylation can achieve both?

I am trying to synthesize a quinoxaline derivative with benzil and diaminobenzene. Literature says i need to use tosyl acid, but i only have tosyl chloride in the lab. What else can i use as an alternative?

I'm converting a tosylate to a bromide but forgot to take some starting material for TLC - which one is likely to be more polar?

EDIT - i meant mesylate, not tosylate (its been a long day)

https://preview.redd.it/g3feohji4m881.png?width=964&format=png&auto=webp&s=fc9ceac1bdb8316b04baeba02c41a0f5747dc3e2

If Pyridine is nucleophilic, does the second step with SN2 occur concurrently during the reaction? I'm talking in the case of primary alcohols. Does pyridine exclusively act as a base?

Hi, just a stupid nomenclature question I have. Given that a 1- substituted pyrrole has no "H" at the 1 position, why is the "1H" still included?

Thanks!

What conditions are needed for the dimethylation of 2,5 dihydroxy benzaldehyde using methyl tosylate and is it possible? I also read that dimethyl carbonate but I can't find any feasible way of making it or any sources for buying it. But I also don't know the reaction conditions needed for that.

Nickel catalysts efficiently promote enantioselective Heck reaction of aryl triflates, mesylates and tosylates in excellent ee values. Asymmetric reductive Heck reaction with a ketal of 2‐cyclopentenone also proceeds well, which is equivalent to conjugate arylation of the enone itself.

Abstract

Nickel‐catalyzed intermolecular Heck reaction of cycloalkenes proceeds well with aryl triflates, mesylates and tosylates in excellent enantiomeric ratios. The asymmetric reductive Heck reaction also works with a 2‐cyclopentenone ketal, which is equivalent to conjugate arylation of the enone itself.

https://ift.tt/2I4AMAs

So after finding this article, I set about finding a use for it. I have discovered 2 main uses for the tosylation. The first is reductions of amino acids to the corresponding alpha methyl amines. And the second is the synthesis of the novel opioid Diampromide (info here, seems to be similar strength to morphine), you could also similarly synthesize the opioid 4-Phenylphenampromide, which is about 60x the potency of morphine.

Both synthesis are outlined here.

Obviously the reduction of the amino acids is fairly inconvenient because it requires quite a strong reducing agent, however I think you could use NaBH4/CuCl2 instead of LAH.

Now of course neither of these synthesis work if the amine is also tosylated, however I find this unlikely due to the synthesis working primarily through lewis acid mechanisms which doesn't tend to work on amines too well. The method in the article selectively tosylated secondary alcohols, and if there is no secondary alcohols it will tosylate primary alcohols, and this is how the propylene glycol is tosylated.

I think that these synthesis have actual justification to be otc due to the availability of the reagents in an otc fashion, and many of the intermediates being easily synthesized (at least in thr opioid synthesis.

Practical application is a higher yielding and enantiomerically selective synthesis of amphetamine (and amt) from an otc source that would be hard to regulate (what are the feds gonna do, regulate amino acids). The opioid synth is fairly practical compared to other opioid synthesis which tend to require advanced precursors (morphine/theabaine or piperidone) and extreme conditions (bomb conditions).

And as usual any thoughts or comments are appreciated.

I'm trying to perform a tosylation reaction with a carbohydrate, with the end goal being eventually- via nucleophilic attack- adding that carbohydrate to a hydroxy group of another compound. Unfortunately, I can't come up with a sugar with only one OH group. This is important, as I don't want to worry about multiple sites being tosylated. What suggestions do you have?

Thanks

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.

Alot of great jokes get posted here! However just because you have a joke, doesn't mean it's a dad joke.

THIS IS NOT ABOUT NSFW, THIS IS ABOUT LONG JOKES, BLONDE JOKES, SEXUAL JOKES, KNOCK KNOCK JOKES, POLITICAL JOKES, ETC BEING POSTED IN A DAD JOKE SUB

Try telling these sexual jokes that get posted here, to your kid and see how your spouse likes it.. if that goes well, Try telling one of your friends kid about your sex life being like Coca cola, first it was normal, than light and now zero , and see if the parents are OK with you telling their kid the "dad joke"

I'm not even referencing the NSFW, I'm saying Dad jokes are corny, and sometimes painful, not sexual

So check out r/jokes for all types of jokes

r/unclejokes for dirty jokes

r/3amjokes for real weird and alot of OC

r/cleandadjokes If your really sick of seeing not dad jokes in r/dadjokes

Punchline !

Edit: this is not a post about NSFW , This is about jokes, knock knock jokes, blonde jokes, political jokes etc being posted in a dad joke sub

Edit 2: don't touch the thermostat

Journal of the American Chemical SocietyDOI: 10.1021/jacs.0c04670

https://ift.tt/2BNfBj9

Do your worst!

How the hell am I suppose to know when it’s raining in Sweden?

Ants don’t even have the concept fathers, let alone a good dad joke. Keep r/ants out of my r/dadjokes.

But no, seriously. I understand rule 7 is great to have intelligent discussion, but sometimes it feels like 1 in 10 posts here is someone getting upset about the jokes on this sub. Let the mods deal with it, they regulate the sub.

Mathematical puns makes me number

They were cooked in Greece.

I'm surprised it hasn't decade.

Now that I listen to albums, I hardly ever leave the house.

Two muffins are in an oven, one muffin looks at the other and says "is it just me, or is it hot in here?"

Then the other muffin says "AHH, TALKING MUFFIN!!!"

The direct copolymerization of epoxides with p‐tosyl isocyanate was achieved in the presence of trialkylborane and polyurethanes could be obtained without the formation of cyclic isocyanurate, in high linear/cyclic and urethane/imidocarbonate selectivity. The reported method provides access to the modification of properties of other polymers, especially aliphatic polycarbonates generated under the same conditions.

Abstract

The direct copolymerization of p‐tosyl isocyanate (TSI) with epoxides, initiated by onium salts in the presence of trialkylborane, to produce polyurethanes is reported. The rate of copolymerization and the (regio)selectivity were investigated in relation to the trialkylborane and the initiator used. Under optimized conditions such copolymerizations have been successfully performed for a wide range of epoxides, including ethylene oxide, propylene oxide, 1‐octene oxide, cyclohexene oxide, and allyl glycidyl ether. These copolymerizations afford a new category of polyurethanes, clear of side products such as cyclic oxazolidinone, isocyanurate, and poly(isocyanate) linkages. The experimental conditions used in this work are compatible with those for the organocatalytic (co)polymerization of other oxygenated monomers and CO2, holding the potential for their terpolymerization with p‐tosyl isocyanate and the development of new materials with unprecedented properties.

https://ift.tt/35AGaV9

The direct copolymerization of p ‐tosyl isocyanate (TSI) with epoxides, initiated by onium salts in the presence of trialkylborane, to produce polyurethanes is reported. The rate of copolymerization and the (regio)selectivity were investigated in relation to the trialkylborane and initiator used. Under optimized conditions such copolymerizations have been successfully performed for a wide range of epoxides, including ethylene oxide, propylene oxide, 1‐octene oxide, cyclohexene oxide, and allyl glycidyl ether. These copolymerizations afford a new category of polyurethanes, clear of side products such as cyclic oxazolidinone, isocyanurate, and poly(isocyanate) linkages. The experimental conditions used in this work are compatible with those for the organocatalytic (co)polymerization of other oxygenated monomers and CO 2 , holding the potential for their terpolymerization with p ‐tosyl isocyanate and the development of new materials with unprecedented properties.

https://ift.tt/3jbd7Mk

Nickel‐catalyzed intermolecular Heck reaction of cycloalkenes proceeds well with aryl triflates, mesylates and tosylates in excellent enantiomeric ratios. The asymmetric reductive Heck reaction also works with a 2‐cyclopentenone ketal,  which is equivalent to conjugate arylation of the enone itself

https://ift.tt/2I4AMAs