
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.
Taizhou Chemedir Biopharm-tech Co., Ltd
Contact:+86 523 86200218
Address:G09, No. 1 Avenue China Medical City, Taizhou,Jiangsu, China
Shandong Ailitong New Material Co.,Ltd
Contact:+86-536-3226266
Address:zhongjia village, putong town , qingzhou city,Shandong Province,China
Wuhan Konberd Biotech Co., Ltd.
Contact:+86-27-87205925
Address:NO.666, Gaoxin Road, Eastlake High-tech zone
Shanghai Korey Pharm Co.,Ltd.(expird)
Contact:021-61840961 021-61840962
Address:No.157,Zhuguang Rd, Qingpu, Shanghai, China
Contact:+86-134-5286-9121
Address:Add: Wing Tuck Commercial Centre, 177-183 Wing Lok Street, Hong Kong,
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)