
Journal of Organometallic Chemistry p. 207 - 230 (1984)
Update date:2022-08-02
Topics:
Lin, Ying-Chih
Mayr, Andreas
Knobler, Carolyn B.
Kaesz, Herbert D.
Primary or secondary aliphatic amines are observed to react with Os3(CO)12 in excess amine or other polar solvents at temperatures in the range -10 to 25 deg C.One mole of CO is evolved and a μ(O,C)-carboxamido complex (1) is isolated in high yield: Os3<μ-H, μ-O=CNR'R>(CO)10 (1a, R = Me, R' = H; 1b, R = R' = Me; 1c, R = n-Pr, R' = H, 1d, R = n-Bu, R' = H; 1e, R = Et, R' = H).The 1H NMR spectrum of 1e indicates the existence of two isomers due to the restricted rotation around the C-N bond of the μ-carboxamido group.Reaction of methyl or ethyl isocyanate with Os3<μ-H>2(CO)10 at room temperature under N2 gives three principal products: a μ(O,N)-formamido complex, Os3<μ-H,μ-OC(H)NR>(CO)10 (2), the μ(O,C)-carboxamido complex, 1, and a μ(C,N)-iminylurethane complex, Os3<μ-H,μ-C(OR')=NR>(CO)10, (4, R' = C(=O)NHR).Product 1 in this reaction arises from isomerization of an intermediate μ(C,N)-hydroxyiminyl complex, Os3(μ-H,μ-C(OH)=NR(CO)10 (3).This complex is isolated upon initial chromatography of the reaction mixture.For the isomerization of 3 to 1, t1/2 17.5 d in CDCl3 solution, Ea 92 kJ/mol.Spectroscopic data indicate that 3 is a mixture of tautomers in ratio of 19/1 in CDCl3: Os3<μ-H,μ-C(OH)=NCH3>(CO)10 (3-enol) and Os3<μ-H,μ-C(=O)N(H)CH3>(CO)10 (3-keto). The structure of 4 has been determined at -158 deg C using a Syntex P<*> computer-automated diffractometer and graphite-monochromatized Mo-Kα radiation.Some 2936 unique reflections with I >3?(I) were used in the refinement to give final discrepancy indices of R = 0.030 and Rw = 0.037.The complex crystallizes in the monoclinic space group P21/c in a cell having the dimensions of a 13.413(3) Angstroem, b 16.712(3) Angstroem, c 9.400(3) Angstroem, and β 95.01(2) deg.The calculated density is 3.06 g cm-3.
Contact:+86-574-87065746
Address:10th Floor, No.787 Baizhang East Road,
Jintan City Mego Chemical Co., Ltd
Contact:+86-0519-82814387
Address:23# Dengguan Town, Jintan, Jiangsu Province, China
SICHUAN TONGSHENG AMINOACID CO.LTD
website:http://www.aminoacid.cc
Contact:86-838-2274206/2850606
Address:Room 1-11-1,No.19 of North TianShan Road,Deyang,Sichuan China
Shanghai Taibao Pharmaceutical Technology Co., Ltd(expird)
Contact:021-52217366
Address:shanghai
Chemsigma International Co.,Ltd.
website:http://www.chemsigma.com
Contact:86-025-58748998
Address:Rm.705, 15th Building,Rd.Xinke II
Doi:10.1021/jo00383a023
(1987)Doi:10.1021/ja00373a047
(1982)Doi:10.1248/cpb.29.3554
(1981)Doi:10.1055/s-2004-831229
(2004)Doi:10.1016/j.bmcl.2004.09.004
(2004)Doi:10.1021/jacs.9b07729
(2019)