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- W2009909064 abstract "Abstract Computations of the Diels–Alder (DA) reactions of azaphosphole representative namely, thiazolo[3,2-d][1,4,2]diazaphosphole with 1,3-butadiene and isoprene at the density functional theory level reveal concerted mechanisms via asynchronous transition states. The activation energies (B3LYP/6-311++G**// B3LYP/6-311G**), 16–19 kcal mol−1, are much smaller than the value (32.57 kcal mol−1) calculated for the DA reaction of the non-phosphorus analogue, imidazo[2,1-b]thiazole with 1,3-butadiene. An electron-withdrawing group at the 3-position of the dienophile enhances both stereo- and regioselectivities, which agree nicely with the experimental values. Inclusion of solvent effect (PCM model) reveals that the stereo- and regioselectivities are not affected appreciably. The relative stabilities of the transition structures corresponding to the endo/exo stereoisomers and meta (P/Me, 1:3)/para (P/Me, 1:4) regioisomers have been rationalized on the basis of the secondary molecular orbital interactions." @default.
- W2009909064 created "2016-06-24" @default.
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- W2009909064 date "2006-02-01" @default.
- W2009909064 modified "2023-09-23" @default.
- W2009909064 title "Origin of the stereo- and regioselectivities in the Diels–Alder reactions of azaphospholes: a DFT investigation" @default.
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- W2009909064 doi "https://doi.org/10.1016/j.tet.2005.11.009" @default.
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