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UnintentionalChaos
International Hazard
Posts: 1454
Registered: 9-12-2006
Location: Mars
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Mood: Nucleophilic
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Really? 3 membered? I would expect a dimeric 6-sided lactone to predominate by a vast majority in that case. I would not expect beta-lactones to be
easy to make either but I see about gamma and delta lactones.
Sorry about my hasty posting. I tend to talk out of my ass when I see GBL or blatant cook posts.
Department of Redundancy Department - Now with paperwork!
'In organic synthesis, we call decomposition products "crap", however this is not a IUPAC approved nomenclature.' -Nicodem
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Nicodem
Super Moderator
Posts: 4230
Registered: 28-12-2004
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3-Membered rings form extraordinarily easily, alpha-lactones included. This is after all the basis of most neighbouring group assisted nucleophilic
substitution, most related being those on alpha-halocarboxylic acids where retention at the chiral centre occurs due to a double SN2 (first an
intramolecular yielding the alpha-lactone and then the intermolecular yielding the final product).
What is truly surprising is that this reaction actually works in the formation of 4-membered rings (beta-lactones) which are cycles that are usually
harder to make (see Justus Liebigs Annalen der Chemie, 619 (1958) 47-53 and 639 (1961) 166-180 for examples of beta-lactones made
this way).
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
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Pomzazed
Hazard to Self
Posts: 57
Registered: 15-9-2008
Location: In th' Lab
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Mood: Acylated
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Look at this;
here's the reference of producing gamma-buterolactone-gamma-carboxylic acid from glutamic acid
http://orgsyn.org/orgsyn/prep.asp?prep=cv7p0099
Don't stare at me making fumes... I'm just experimenting with some gas...
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AndersHoveland
Hazard to Other Members, due to repeated speculation and posting of untested highly dangerous procedures!
Posts: 1986
Registered: 2-3-2011
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Diazotization. NaNO2 + HBr (and heating) will substitute the amino group with a bromine group. The bromine can easily be substituted off by any
nucleophile.
Ever heard of the Sandmeyer reaction?
I'm not saying let's go kill all the stupid people...I'm just saying lets remove all the warning labels and let the problem sort itself out.
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madscientist
National Hazard
Posts: 962
Registered: 19-5-2002
Location: American Midwest
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http://pubs.acs.org/doi/abs/10.1021/jo060316a
FYI, the Sandmeyer is not general to aliphatic amines, this is a special case exception.
[Edited on 27-3-2013 by madscientist]
I weep at the sight of flaming acetic anhydride.
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