Quaternary ammonium halides as powerful lanthanide shift donors

Seeman, Jeffrey I.; Bassfield, Ronald L.

doi:10.1021/jo00433a035

Cited by 17 publications

(12 citation statements)

References 3 publications

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“…During his travels, Nozoe brought with him his autograph books in which he collected 1179 pages of autographs from well over 4000 chemists and their students and even their families. [4][5][6] These autograph books are now being published in their entirety in 15 consecutive issues of The Chemical Record. The first segment of 68 pages from 1953 appeared in the October 2012 issue of this journal along with a specially designed web presence (see: http://www.tcr.wiley-vch.de/ nozoe).…”

Section: Introductionmentioning

confidence: 99%

Tetsuo Nozoe: The World Traveler, On a Determined Trajectory

Seeman

2014

The Chemical Record

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Tetsuo Nozoe embarked on many grand tours during his lifetime. The Grand Tours of late 1966 are among his most impressive, spanning Europe and North America with short trips back to Japan in between. Jeffrey I. Seeman takes us along these tours, showing how Nozoe was able to squeeze in a breathtaking number of visits into his “wish list” of organic chemistry, at a time before internet and mobile phones. This Essay and the interactive website that accompanies the Nozoe Autograph Book project are available free‐access for at least a three‐year period at http://www.tcr.wiley-vch.de/nozoe.

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Section: Introductionmentioning

confidence: 99%

Tetsuo Nozoe: The World Traveler, On a Determined Trajectory

Seeman

2014

The Chemical Record

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“…It has been postulated that the mechanism by which L n ( f~d )~ complexes cause shifts in the spectra of organic salts involves the formation of the anionic species [Ln(fod),X]-(X = original anion of the organic salt) (eq 2 ) (26-28, [50][51][52][53][54][55][56]. formation of such a precipitate was obvious from both the volume of insoluble material and unmistakable appearance of the silver halide.…”

Section: Resultsmentioning

confidence: 99%

Organic-soluble lanthanide nuclear magnetic resonance shift reagents for sulfonium and isothiouronium salts

Wenzel¹,

Zaia²

1987

Anal. Chem.

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London, A 1981, 300, 15-41. Wilson, M. A.; Rottendorf. H.; Collin, P. J.; Vassallo, A. M.; Barron, P. F. fuel 1982, 6 1 , 321-328. Schafer, H. N. S. Fuel 1972, 5 1 , 4-9. Thurman, E. M.; Malcolm, R. L. In Aquatic and Terrestrial Humic Materials; Ann Arbor Science: Ann Arbor, MI, 1983; pp 1-24. Oades. J. M.; Vassallo, A. M.; Waters, A. G.; Wilson, M. A. Aust. J . Soil Res ., in press. Wilson, M. A.; Collin, P. J.; Pugmire, R. J.; Grant, D. M . Fuel 1982, 6 1 , 959-967. Ollivier, P.; Gerstein, B. C. Carbon 1984, 22, 409-412. Pugmire, R. J.; Zilm. K. W.; Grant, D. M.; Larter, S. R.; Allen, J.; Senftle, J. R.; Davis, A.; Spackman, W. ACS Symp. Ser. 1981, No. Pugmire, R. J.; Zilm, K. W.; Woolfenden, W. R.; Grant, D. M.; Dyrkacz, G. R.; Bloomquist, C. A. A,; Horwitz, E. P. Org. Geochem. 1982, 4 , 79-84. Pugmire, R. J.; Woolfenden, W. R.; Mayne, C. L.; Karas, J.; Grant, D. M. ACS Symp. Ser. 1984, No. 252, 79-97. Wilson, M. A.; Pugmlre, R. J.; Karas, J.; Alemany, L. B.; Woolfenden, W. R.; Grant, D. M.; Given, P. H. Anal. Chem. 1984, 56, 933-943. Zilm, K. W.; Pugmire, R. J.; Larter, S. R.; Alien, J.; Grant, D. M. fuel 1981, 60, 717-722. Karas, J.; Pugmire, R. J.; Woolfenden. W. R.; Grant, D. M.; Blair, S. 6,6,7,7,8,8,8-heptafiuoro-2,2-dlmethyl-3,5-octanedlone) are eff ectlve organlc-soluble nuclear magnetlc resonance shlft reagents for sulfonlum and lsothlouronlum salts. The shlft reagent Is formed in solution from Ln(fod), and Ag(fod) or K(fod). The selectlon of Ag(fod) or K(fod) In forming the shift reagent is dependent on the anion of the organic salt. Ag(fod) Is more effectlve wlth halide salts, whereas K(fod) is preferred with tetrafluoroborate salts. Resolution of diastereotopic hydrogen atoms was observed In the shifted spectra of certain substrates. Enantlomerlc resoiutlon was obtained In the spectrum of sec-butyllsothlouronium chlorkle wlth a chlrai shift reagent. The reagents can be employed In solvents such as chloroform and benzene. Int. Lanthanide complexes of the formula [Ln(fod),]-(fod, EXPERIMENTAL SECTIONReagents. The compounds 1-iodobutane, iodomethane, 1bromopentane, 1-bromononane, I-chlorobutane, benzyl chloride,

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“…The most evident route to ( 2 ) is v i a deuteroiodomethylation of the corresponding secondary amine ( 2 ) . One problem with such a route is the formation of HI in the reaction, leading in part to protbnation of the pyrrolidine nitrogen N-CD3 Labelled Nicotine and Nicotine Analogues 389 of either unreacted nornicotine or the initial product, nicotine.…”

Section: Resultsmentioning

confidence: 99%

“…N-CD3 Labelled Nicotine and Nicotine Analogues 391 Alkylation of 2-(4-methylphenyl)-l-pyrroline ( 2 ) with CD31 in acetonitrile was followed by tlc and a spot of low Rf grew in importance concurrent with a decrease in intensity of the spot corresponding to the starting imine. After thirteen days, the precipitated iminium salt was reduced with sodium cyanoborohydride.…”

Section: "2mentioning

confidence: 99%