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Post 461467 (missing)
(Rhodium: "post numbers", General Discourse) then go back and edit your posts.
Methods:
A:
R-SO2.OH + C3N3Cl3 ---> R-SO2.Cl + C3N3Cl2.OH
B:
R-SO2.ONa + C3N3Cl3 ---> R-SO2.Cl + C3N3Cl2.ONa
Mechanism:
R-SO2.OH + cyanuric acid + NEt3 ---->
R-SO2.O-C(Cl)(N3Cl2C2) + HN+Et3 ---->
R-SO2.Cl + N3Cl2C3.O- + HN+Et3
Prepared sulfonyl chlorides:
Yield:
R-SO3H Method CC Dist
----------------------------------
Me- A - 47%
Et- B - 74%
Me(CH2)3- B - 86%
Me(CH2)4- B - 70%
Benzene- A 90% 86%
B 94% -
p-Toluene- A 96% 94%
B 94% -
p-xylene- A 74% 70%
mesitylene- A 64% -
B 94% -
p-chlorobenzene A 76% -
B 96% -
p-acetaminobenz. A 66% -
B 70% -
B-napthalene A 88% -
B 89% -
refs on request, have fun guys.
Post 382242 (https://www.thevespiary.org/talk/index.php?topic=11582.msg38224200#msg38224200)
(Rhodium: "trichloroisocyanuric acid - cyanuric chloride", Novel Discourse)
In principle any chemical reaction where ions or ionic intermediates are involved in any form can be modified or improved through crown compounds. Among others, nucleophilic substitutions (e.g. halogen- and pseudohalogen substitutions, O-, N-, S-alkylations), reactions with carbanions, C-C bond formation (e.g. Darzen's, Knoevenagel condensations etc.), additions, eliminations, carbene generation, gas extrusions (N2, CO2), oxidations, reductions (dissolving metal, metal hydrides), rearrangements (Favorskii, Cope), isomerizations, and polymerisations are concerned. Further application fields of crown compounds are in the range of macrolide synthesis, of organo metal and protecting group reactions as well as phosphorous and silicon chemistry.
for further reading check the above publication, and also:
monographs
Phase transfer catalysts, principle and techniques, W.P. Weber & G.W.Gokel, New York, San Francisco, London 1978
Phase transfer catalysis, principles and techniques, C.M.Starks & C.Liotta, Concepts in Organic Chemistry 4, Springer-Verlag, Berlin, Heidelberg, New York 1977
Compendium of phase transfer reaction and related synthetic methods, W.E.Keller, Fluka AG, Buchs, Switzerland 1979
Phase transfer catalysis, monographs in modern chemistry 11, E.V.Dehmlow & S.S.Dehmlow, Verlag Chemie, Weinheim 1980 and 1983
Reviews
Crown ether chemistry: principles and applications, G.W.Gokel & H.D.Durst, Aldrichimica Acta 9, 3 (1976)
Principles and synthetic applications in crown ether chemistry, G.W.Gokel & H.D.Durst, Synthesis, 168 (1976)
Crown ethers, A.C.Knipe, J. Chem. Educ. 53, 618 (1976)
Neutrale organische komplex-liganden und ihre alkalikomplexe II - Krönenaether, cryptanden als reagenzien und katalysatoren (Teil B), E.Weber & F.Vögtle, Kontakte (Merck) 3, 36 (1977)
Progress in crown ether chemistry (part IVC), E.Weber, Kontakte (Merck), 1, 24 (1982)
Progress in crown ether chemistry (part IVD): new types of neutral ligand-assisted chemical reactions, E.Weber, Kontakte (Merck), 1, 38 (1983)
Phase transfer catalysis, G.W.Gokel, E.Weber:
(part I: general principles), J.Chem.Educ. 55, 350, (1978)
(part II: synthetic applications), J.Chem.Educ. 55, 429 (1978)
Macrocyclic polyethers - application to organic reactions, K.Koga, Yuki Gosei Kagaku Kyokai Shi, 33, 163 (1975)
Fortschritte der phasentransfer-katalyse, E.V.Dehmlow, Angew. Chem. 89, 521 (1977) and Angew. Chem. Int. Eng. Ed., 16, 493 (1977)
Application of macrocyclic polydentate ligands to synthetic transformations, C.L.Liotta, Synthetic multidentate macrocyclic compounds, p. 111, Academic Press, San Francisco, London, 1978
Organic transformations mediated by macrocyclic multidentate ligands, C.L.Liotta, The chemistry of functional groups, suppl. E, part 1, p. 157, Wiley, London, 1980
Phase-transfer catalysed reactions, F.Montanari et al., Host guest complex chemistry II, Top. Curr. Chem., p. 147, Springer-Verlag, Berlin, Heidelberg, New York, 1982
The present use and the possibilities of phase transfer catalysis in drug synthesis, P.Cocagne et al., Heterocycles 20, 1379 (1983)
It isn't made, it is bought cheaply as an industrial chemical. You don't want to try even, as it is manufactured from hydrogen cyanide and chlorine gas at elevated temperatures
Exactly. You cannot make it. And most people cannot buy it. They're left out, their bodies shaking in the cold wind that blows along the snowy streets. Their hands stiff until the alcohol brings along some warm thoughts of better days - a summer they will never see.
Someday the source will be with me. Oh no - it was just another nip from the bottle of everclear.
--psyloxy--
"I'd rather be a small part of something great than a big part of a pile of shit" - Josh Homme