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kiddie khemistry kiddie khemistry its time for that science league this organic chemistry blog is mainly dedicated to breaking down total synthesis and methodology papers with a side of chemistry humor saturday april 3 2010 chemistry mad libs round 2 here s a little snippit i ve found in science in this scenario a adjective catalyst might verb with a protonated substrate through the noun and induce enantioselectivity in adverb addition reactions to the adjective electrophile through specific adjective interactions with the charged noun this is what i ended up with in this scenario a hairy catalyst might exercise with a protonated substrate through the fish tank and induce enantioselectivity in aggresive addition reactions to the bloated electrophile through specific sneaky interactions with the charged rattle snake this is the original in this scenario a chiral catalyst might associate with a protonated substrate through the counteranion and induce enantioselectivity in nucleophilic addition reactions to the cationic electrophile through specific secondary interactions with the charged species h xu s j zuend m g woll y tao e n jacobsen asymmetric cooperative catalysis of strong brønsted acid promoted reactions using chiral ureas science 2010 327 986 990 posted by deezy7 at 7 42 am no comments wednesday march 24 2010 chemistry mad libs first edition when the oxygen does the noun attack it forms a adjective bond with noun the reaction was run in a size noun where it was spun and verb after 3 hours it was quenched with ammonium chloride mine when the oxygen does the dolphin attack it forms a swirly bond with your mom the reaction was run in a huge van where it was spun and squeezed after 3 hours it was quenched with ammonium chloride im excited about writing these more often check back for more laz posted by deezy7 at 12 01 pm 1 comment saturday december 26 2009 where i ve been sorry about the lack of posts lately ive been really busy with this fall semester getting mediocre grades in my grade boosting semester i guess you lose focus when you don t have any chemistry classes well as of right now i m signing up for reu projects all across the nation and some even jump a small pool of water to places where people talk funny but hopefully then i can get back into reading papers and crankin out some posts until then you can listen to my music www myspace com kiddiekhem hope you like it posted by deezy7 at 10 25 pm no comments wednesday july 29 2009 pranks pranks are fun and can be a fun way to add some spice to your lab but how can you implement them without getting caught and hurting the science whether you re acting like you didnt bring the compound to the spectra lab when your in a group or something more complicated like what ive got for you today its always interesting to see what happens this prank was executed by simply setting it on a lab member s desk i followed up by asking how weird was the tungsten reaction he answered with yes it was somewhat hard to follow the mechanism though hes not an organo metallic guy well now ive got a lab partner that thinks hes a pro at terminal alkane coupling id say it worked out well voice any lab pranks youve done in the comments posted by deezy7 at 8 31 am 2 comments friday july 10 2009 enantioselective total synthesis of the potent anti inflammatory myrrhanol a victoriano domingo lucia silva horacio r dieguez jesus f arteagas jose f quilez del moral and alejandro f barreo link to the paper so this latest taste of science is freshly out of spain the main reaction here which caught my eye was the ti catalyzed radical cyclization forming a few new bonds and creating 3 stereocenters some other good science a nice negishi carbometalation a suzuki using 9 bbn and a nice epoxidation followed by reduction well they started early with the ti cyclization it has a radical mechanism where the titanium catalyzes a heterolitic bond breakage between the oxygen in the epoxide and the more highly substituted carbon in which its attached to they formed this epoxide using dmap this carbon then attacks the neighboring sp2 carbon to form a chair generating the sterocenter this then pushes one electron from the pi bond over to then react with the other alkene in the same chair which then eliminates giving the lone electron back to the titanium quite the proposed mechanism but i love the end product of this reaction it reminds me of the excitement i once had from studying the diels alder and the two bonds and stereocenters it formed here s the paper they referenced on this step pdf the next reaction in their synthesis was their chiral epoxidation it looks as though the chirality was obtained via the steric bulk of the adjacent methyl and other parts of the ring structure after this they simply used lialh4 to reduce the epoxide on the less substuted carbon affording the alcohol on the tertiary carbon here is a reaction i had to do some reading on to understand the negishi carbometalation has a very interesting mechanism essentially the zirconium acts as a total theif and steals the aluminum s methyl along with its electrons from the bond then stabilizes it with its two chlorine it then sits down onto the alkyne similar to how you see hcl act with the negative chlorine or in this case methyl going to the more substituted carbon after this the zirconium and the aluminum switch bonds the methyl on the aluminum and the bond from the alkene on the zirconium finnaly they add i2 to t solution one iodine bonding to the aluminum and one to the alkene this explanation is pretty rough around the edges so if you want to check out the paper yourself here it is one of the later reactions of this paper was the suzuki using 9 bbn here the 9 bbn was used to reduce the alkyne and place a steric boron group on the terminal carbon this step was followed with a pd coupling with the vinyl idoide i like the versatility of this step and its getting me to think about different ways to incorporate boron groups into various structures lots of fun organometalics in this one posted by deezy7 at 11 38 am no comments tuesday july 7 2009 big adventure in little city so now that i ve gotten that jackie chan sounding title out of the way ill get to the story so the plan was to play tunes and skype untill the sun began to set get on a city bus and take it round trip to see the city soon i was wandering around the medschool looking for the south bus things seemed to look a little different now that it was dark and i ended up spending a decent amount of time wandering outside of the medschool i was thrilled with that though it worked out perfect saw all of the buildings from a different road which look alot prettier than the normal view ended up in a cove within the medschool with some very pretty locked doors and then when i broke out of it and found the stop the hospital helicopter was taking off it was dark now and it was soo coool snagged a video on the phone it wasn t long untill i was hopping on the 935 bus but before that i met a guy that was shot 4 times the initial bus ride was awesome it had layered rows and i got on a seat near the back which sat alot higher than the rest to get a better view okay well now im going to start telling the story from someone who has already finished the trip and understands what the heck happened at the monroe stop the bus driver got out and got into a car that was sitting there as we pulled up she was in that parked car for 10 minutes untill a cop walked up i have no clue what was said but 5 minutes later the bus rejoined its course soon we were driving through downtown tall buildings lots of lights it was gorgeous when we got to the downtown stop some people were exchanged and then a bus driver got on he spoke with her for around five minutes in what seemed to be a heated conversation then we headed north of the city lots of new unseen buildings the beer factory from a new side and this is where most of the people on the bus requested stops after every one else got off she ended up pulling into a wegmans parking lot behind a parked bus announcing this is the last stop soon i was questioning her how this was the last stop and not a round trip back to the hospital she said no it doesn t work like that and eventually just gave whatever as an answer im guessing that talk with the other bus driver may have gotten her angry well i got off into this unknown area and looked around noticing there was a bus stop sign none of the routes on the sign were for south instead of getting stressed out i decided there were worse places to get stranded and decided to make a trip into the wegmans a local grocery store there i got some delicious mango slices which helped cool me down and ended up carrying me to the end of the trip after wandering around the store and doing some munchin headed back to the bus stop and met a new bus driver i asked him if he knew where i was and told him how i became stranded we chatted for a bit and he said he was headed downtown where i could get on another bus to go to strong i sat on the front seat and we talked for a good bit of the bus ride he told me alot about rochester and that his hometown was actually very close to my own after seeing a completely new area of the town and how freakin cool the handicapped lift for a bus is we made it downtown i got on the 19 like the previous bus driver instructed but this time i made sure we were headed to strong hospital he said we were headed to strong but that itll be a while since it goes through the university i was exuberant the bus ended up taking me within 2 minutes of the dorm i stay in it was awesome posted by deezy7 at 8 51 am 3 comments saturday july 4 2009 a versatile route to the tulearin class of macro lactones synthesis of a stereoisomer of tulerarin a alexander l mandel veronique bellosta dennis p curran and janine cossy link to the pdf here is a fun little paper out of paris this paper really makes up for the lack of reactions you saw in the last paper totaling about 18 some being deprotections and protections hence the about the science begins with a julia kocienski olefination here they used a sulfone with a phenyltetrazolyl group on it to bring forth the trans alkene the mechanism involves potassium bonding to the non conjugated carbon adjacent to the sulfone and an attack on the aldehyde then after a series of elimations it gives off sulfur dioxide and the phenyltetrazolyl after the sharpless they used dibal h to reduce the ester within the lactone into an aldehyde and then they used a methyl phosphine to afford the terminal alkene which becomes very important later in the synthesis here they used a benzylthiazolidine thione group known as the crimmins chiral auxiliary with specific conditions in this aldol addition to attain specific stereochemistry after that they do a simple protection and then remove the benzylthiazolidine thione group using hydroxide and peroxide finally completing the scaffolding they carry out a ring closing metathasis using grubbs first generation they also attempted the reaction using other catalysts but gave side products or did not react at all some nice science liked the julia and seeing the crimmins in action was nice posted by deezy7 at 5 18 pm no comments older posts home subscribe to posts atom followers blog archive 2010 2 april 1 chemistry mad libs round 2 march 1 2009 11 december 1 july 6 june 4 about me deezy7 any questions about the blog or anything at all feel free to shoot me an e mail mdp8889 aol com view my complete profile links carbon based curiosities chemical sabbatical chemistry blog chemistry world blog labnotebook lamentations on chemistry making graphite work o and o chemistry org prep daily relm of organic totally synthetic