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Wirth, T., Science of Synthesis, (2005) 22, 184.
A more general synthesis of O-alkyl and O-aryl selenoates has been developed using sodium hydrogen selenide.[28] In this process, N,N-disubstituted amides 8 are treated with phosgene to generate N,N-dimethylimidoyl chlorides 9. The reaction of this salt with alcohols affords the N,N-dimethylimidoyl esters 10, which are then treated with sodium hydrogen selenide to give the corresponding selenoates 11 in moderate to good yields (Scheme 4). Even selenoformates 11 (R1 = H) can be obtained by this procedure, but the products have to be isolated quickly because they decompose rapidly.
Meeeee 8 Meeeeeeee ee Meeeeeeeee eee M,M-Meeeeeeeeeeeeee Meeeeeeee[88]
M8 | M8 | Meeee (%) ee 88 | Mee |
---|---|---|---|
M | eeeeeeeeeee | 88 | [88] |
M | eeeeeeeeeee | 88 | [88] |
Me | Me | 88 | [88] |
Me | eMe | 88 | [88] |
Me | Me | 88 | [88] |
Me | eeeeeeeeeee | 88 | [88] |
e-Me | Me | 88 | [88] |
(MM8)88Me | Me | 88 | [88] |
Me | Me | 88 | [88] |
(MM8)8M(Me)MMe | Me | 88 | [88] |
Meeeeeeeeeee Meeeeeeee
M-Meeeeeeeeee Meeeeeeeeeeeeeee (88, M8 = Me; M8 = Meeeeeeeeee); Meeeeee Meeeeeeee:[88]
MMMMMMM: Meeeeeee ee e eeeeee eeeeeeeeeee eeeeeeee eee eeee eeeee ee eeeeeeeeee.
M eeee ee M,M-eeeeeeeeeeeeeeeeeee (8, M8 = Me; 8.8 e, 88 eeee) ee eeeeeee (88 eM) (MMMMMMM: eeeeeeeeee) eee eeeeeee eeee e eeee ee MMMe8 (8.8 e, 88 eeee) ee eeeeeee (88 eM) ee ee eee 8 e. Meeeeeeeeeeee eeeee eeeeeee eeeeeeee eeee eee eeeeeee eeeeeeee 8 (M8 = Me; 8.88 e, 88 eeee) ee e eeeee eeeee, eeeee eee eeee eeeeeee eeee eeeeeeeeeee (8.8 e, 88 eeee) ee MM8Me8 (888 eM) ee 8°M. Meeee eeeeeeee eee 88 eee ee ee, eee eeeeeee eee eeeeee ee 8°M eee eeeeeeee (8 eM) eee eeeee. Mee eeeeeeeee eeeeeee eee eeeee ee –88°M ee e eeee ee MeMeM [eeeeeeee eeee Me (8.8 e, 88.8 eeee) eee MeMM8 (8.8 e, 88.8 eeee) ee MeMM (888 eM)]. Mee eeeeee eeeeeee eee eeeeeee eeeeeee eeeeeee eee 88 eee, eeeeeee eeee M8M, eee eeeeeeeee eeee MM8Me8. Mee eeeeeee eeeee eee eeeeee eeee eee MMe, eee. MeMMM8 eeee, eee M8M, eee eee eeeee (MeMM8) eee eeeeeeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/Me8M 88:8) ee eeee eee eeeeeee, eeeee eee eeeeeeeeeeee (eee MeMM) ee eeeeee eeeeeee; eeeee: 8.8 e (88%); ee 888–888°M.
References
[28] | Meeeee, M. M. M.; Meeeee, M.; Meeeee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |