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Synthesis and Structural Study of Novel Selenation Derivatives of N, N ‐Dialkylcyanamides
Author(s) -
Hua Guoxiong,
Du Junyi,
Slawin Alexandra M. Z.,
Woollins J. Derek
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201601577
Subject(s) - diselenide , chemistry , reagent , cycloaddition , toluene , hydrolysis , spectroscopy , nuclear magnetic resonance spectroscopy , medicinal chemistry , mass spectrometry , crystal structure , organic chemistry , catalysis , selenium , chromatography , physics , quantum mechanics
The reaction of 2,4‐bis(phenyl)‐1,3‐diselenadiphosphetane‐2,4‐diselenide {[PhP(Se)( μ ‐Se)] 2 , Woollins’ reagent, WR } with N, N ‐dialkylcyanamides 1–3 in refluxing toluene solution led to the corresponding [2+3] cycloaddition products 4‐dialkylamino‐2,5‐diphenyl‐1,3,2,5‐selenazadiphosphole 2,5‐diselenides 4–6 in good yields, the latter were further treated with water resulting in the corresponding hydrolysis derivatives dialkyl‐selenoureas 7–9 , and phosphinodiselenoates 10 and 11 . Selenourea 7 could be transferred into 1,3‐selenazol‐2‐amines 12–15 in excellent yields by further cyclization with four different α ‐haloketones. All new compounds have been characterized by IR spectroscopy, multi‐NMR ( 1 H, 13 C, 31 P, 77 Se) spectroscopy and accurate mass measurement. The single crystal X‐ray structural features of nine new compounds are also discussed.