ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Pyrylium Compounds. XXVIII. Specifically Deuterated Carbo- and heterocycles via 2,4,6-Triaryl[3,5-2H2]pyrylium SaltsOn heating with catalytic amounts of bases(e.g. triethyl amine) in deuterated alcohols such as methan[2H]ol or ethan[2H]ol pseudobases of 2, 4, 6-triarylpyrylium salts 1 undergo fast1H/2H isotopic exchange reaction affording 1, 3, 5-triaryl[2, 4, 4-2H3]pent-2-ene-1,5-diones which with [2H] perchloric acid give highly deuterated 2, 4, 6-triaryl-[3, 5-2H] pyrylium perchlorates 8. These salts are obtainable also directly from 1 through a one-pot procedure by ring opening of the latter with deuterium oxide under the above-mentioned1H/2H isotopic exchange conditions followed by recyclization of the formed 1, 3, 5-triaryl[2, 4, 4-2H3]pent-2-ene-1, 5-diones with [2H]ClO4. Ring transformations of 2, 4, 6-triphenyl[3, 5-2H2]pyrylium perchlorate (8a) to 2, 4, 6-triphenyl[3, 5-2H2]nitrobenzene (9) 2, 4, 6-triphenyl[3, 5-2H2]pyridine (10), 1, 2, 4, 6-tetraphenyl[3, 5-2H2]pyrydinium perchlorate(11), 2, 4, 6-triphencyl[3, 5-2H2]thiopyrylium perchlorate(12), 2-benzoyl-3, 5-diphenyl[4-2H]furan (13), and 3, 5, 7-triphenyl-[4, 4, 6-2H3]4H-1, 2-diazepin (14) demonstrate the usability of pyrylium salts of type 8 as starting materials for syntheses of specifically deuterated carbo- and hetrocycles.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19853270402
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