Studies on the azidoazomethine-tetrazole equilibrium

The structure of an unusual disulfide, formed from reaction between a sulfene–amine zwitterion and thionyl chloride

“…The conversion 7 + 8 is supported by the work of Krubsack and co-workers (2),5 whereas the desulfonylation 8 + 9 has a precedent in work by Fusco et 01. (19). Reduction of sulfenyl chlorides to disulfides (9 + 3) is amply documented (8).…”

Use of 1,5‐Diaminotetrazole in the Synthesis of Some Fused Heterocyclic Compounds.

“…or an az1 o unctiOn • may e considered as existing in a tautomeric equilibrium with tetrazole system 20 . Consequently, it was of interest to develop of synthetic methods for construction of tetrazolo nucleus.…”

Sulfonylation of alkylidene- and arylidenephosphoranes. An unexpected rearrangement

“…A fraction of 0.26 g of 16c was obtained (contaminated with some 15c). Recrystallization from chloroform-ether yielded 47 mg (0.12 mmol, 1.3%) of pure 16c: mp 222-223.5°; mass spectrum (70 eV, 180°, direct inlet system) m/e (rel abundance >5) 410 (9), 395 (100), 316 (9), 315 (28), 301 (20), 261 (5), 201 (5), 185 (5), 183 (16), 108 (9), 91 (5), 57 (5), 43 (5), 41 (10) a-Ethylsulfonylneopentylidenetriphenylphosphorane (16d, Expt 17). A solution of neopentylidenetriphenylphosphorane (prepared from 9.20 g, 20 mmol, of the corresponding phosphonium iodide, see above) in tetrahydrofuran (500 ml) under nitrogen was cooled to -90°.…”

“…Triphenylphosphine (70 mg) was added and the reduction reaction was followed by nmr at about 40°. The peak at 7.2 (CH in 5) disappeared al- (10) D. Diller and F. Bergmann, J. Org. Chem., 37, 2147 (1972).…”