mayorfixie

@TomCaron I was a high schooler 30 years ago following Boston sports, and I remember watching you and thinking “this guy does it better and is more entertaining than anyone else I’ve seen. I hope he sticks around.” I’m not surprised at all I got my wish. Congrats on 30 years!

30 years ago today I began my career at NESN. Three decades covering greatest teams in Boston history, with some of the best people you could possibly work with, for the greatest fans in the world. Thanks to everyone who’s been along for the ride. And we’re not done yet.

@awhspeed Ugh, you’ve made me remember the time I prepared the Greico reagent and thought “the starting material and product are both strongly scented which means organo-selenium is now inside my body and those are two facts I didn’t want to learn today”.

More slides!

@awhspeed Sorry, I only have the one from the 200 mg of diethyl ether hydroperoxide I isolated and purified off of a column as an unknown spot on the reaction TLC 😬 That was a shocking NMR analysis, and the quickest I ever re-diluted an isolated product.

Does anyone have a good reference for the 1H NMR of THF hydroperoxide?

@awhspeed However! If you don’t know the increased reactivity of thiazolidine thiones compared to d’one, it could pose a problem. I recall a labmate of ours trying to protect the aldol pdt with TBSCl/imidazole was actually cleaving the auxiliary through imid-mediated (!) acyl transfer.

@awhspeed I have to say, the yellow color was much appreciated on column chromatography, and the readily cleavable (ie no exo-cyclic hydrolysis/cleavage) nature is pretty great compared to d’one. (Blasphemy!)

A fun slide to make, got to use some photos from my PhD.

@awhspeed I recall about 2/3 of the way through my time in the lab that the 30+ year old supply of tributylborane ran out. Off chance a new lot of “rolled your own” Bu2BOTf wasn’t up to snuff?Seems far-fetched, but offering a possible, not probable explanation. Agree your result is weird!

In reviewing some notes on boron aldols, I was reminded of a very puzzling event from my PhD, where I had a fragment coupling that worked, then stopped working. To this day, I don't know what happened. Fortunately changing to a different reagent worked reliably.

@awhspeed @DrLCsquare Seconded.

@DrLCsquare Yup

When someone calls a conjugate addition of a hetero-atom a « Michael addition » in front of a Dave Evans grad…

@awhspeed This is amazing. I am astonished I (we) never heard this story. I’d have thought this would have been part of group-adjacent lore.

Funny, I never knew they got the wrong Donald Cram the first (and second) time phoning from Stockholm: youtube.com/watch?v=tNoJL6…

@awhspeed More (in case you’re still in the market): Almost famous Lost in translation Adaptation Eternal sunshine of the spotless mind O brother where art thou Master and commander Touching the void Mean girls Zoolander Just a random smattering of movies I enjoyed. No particular order.

Last weekend was driving with a friend and we got stuck behind a logging truck, and got to reminiscing about the "Final Destination" franchise. Found them on Netflix this weekend, and they are really worse than I remember. Any good movie recommendations from the early 2000s?

@awhspeed 28 days later (do you like zombie movies?)

@awhspeed Devils and details…why IMO it takes a certain “type” of person to be a (good) scientist. (Well done, btw!)

Good lesson on being observant, and purifying. My crude mixture looked non-uniform. Here are 2 NMR specta made up of samples taken from different parts of the same flask of a crude rxn mixture. Top spectrum is from base of flask, bottom spectrum is from the side.

@awhspeed Good luck! (What class??)

T minus 30 minutes to the first class I will have taught in over a year:

@awhspeed @BagPhos @XMa75870843 I’ve used a chelator workup for titanium rxns with great success. Quench with THEED (CAS# 140-07-8) and stir for an hour or so, then partition between NH4OH (say 1M) and organic. Everything in solution IIRC.

@BagPhos @XMa75870843 We use Ti(OEt)4 a lot. We quench with aqueous KOH, which makes something pretty granular, and have a "Ti filter", which is very wide, and we don't care that has a coating of TiO2. Also sonication will usually free Ti residues from glass, though we also keep Ti glassware!

@MarkLautens @MatthewHorwitz1 @AmerChemSociety The tradition continued through my time in the group (‘02-‘08) and I’m privileged to have a great collection of theses as well (some hard bound, some digital files).

@MatthewHorwitz1 @AmerChemSociety Our funding agency did not require a thesis but the group culture was to produce a bound thesis. In my day each grad student gave a copy of their thesis to current group members when they graduated. I have some wonderful thesis from some amazing doctoral graduates.

As I prepare for a short talk at the Evans Memorial Symposium in SF ⁦@AmerChemSociety⁩ my mind and memories cast back to 1987 and my postdoc with DAE.

@awhspeed @Chemjobber What does is mean if I’m a 12?

@Chemjobber 17

4

@14Kountz And I say this as someone who truly believes in the importance of the microbiome. It’s going to end up as a validated drug target many times over, but it’s going to take a while - perhaps decades - to get to where perception and reality find equilibrium.

@14Kountz …that will get us back to the idea of the microbiome as a drug target. Given 10s of companies and billons of $ investment, and only one successful Ph 3 trial (Seres) it’s going to be a while before over-hyped reporting can do more damage than the industry has done to itself

@awhspeed I tend to go with the NYT wirecutter recommendations, and a dehumidifier is no exception. Been going strong for 4years and counting in the basement. nytimes.com/wirecutter/rev…

Anyone have a good suggestion for a dehumidifier for a 1 bedroom apartment?

@NaOHBartfield So 70% protecting group by mass then. Only 30% substrate disposed 😛

Lab cleanout: pouring TBDPS pleuromutilin down the waste