By F.G.A. Stone, Robert West (Eds.)
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Additional info for Advances in Organometallic Chemistry, Vol. 32
Me2 t (CO)5C r S = C \ S-C-NMe2 + ,NMe2 (C0I5CrS=C II 222 S 223 \ S -C- I1 0 N Me2 49 Organosulfur and Organoselenium Organometallic Compounds The anionic carbene complexes of type 225 ( M = Cr, W ) simply add ClCHS(CH,),S to form 226, but they rearrange to the vinylcarbene complex 227 with loss of thiophenol when treated with PhCH(SPh)Cl (105). --+ (CO) M=C 5 \ (CO)M=C /OEt 5 CHL ‘CH2 I 225 226 225 t u s h S PhCH(SPh1CI _j C0,Cr /O Et 9 =C + HSPh Ph H 2 27 The anionic adducts 186 abstract R2E2+from the disulfide or diselenide, R2E2E2R2,which adds to the (Y carbon of the thioketene function, to form the unsaturated dithioester complexes of type 228 (84).
Essentially the rearrangement entails a double consecutive internal carbonylation. Neutral heterometallacyclic carbene complexes (111, L = CO, phosphine, or phosphite ligands) result 0 Et 110 Ill R' on further alkylation. Addition of a-deprotonated thioacetals or sulfides to [ M(CO),] (M = Cr or W) also causes cyclization; however, in this case an intermediate carbene is formed, and CO insertion into a metal-carbene bond effects the second carbonylation. The same type of cyclization occurs with LiCH(SR1)R2 [R' = Ph, RZ= SPh; R1R2= -(CH d3S-I and [Cr(CO),CNPh], but, instead of a carbonylation in the second step of the transformation, a formal insertion of isocyanide into the metal-carbene bond occurs, to afford a phenylaminocarbene-thioetherchelate (103).
Thiols A number of reactions of organothiols with complexes of alkoxycarbenes, isocyanides, or thiocarbonyls, leading to thiocarbene complexes, have been reviewed (4,125,126). Further related examples include the conversion of a chlorocarbene to a dithiocarbene by reaction of the ruthenium complex 154 with RSH (R = Me, ptolyl) or HSCH2CH2SHto give the dithiocarbene compounds 155 and 156 (82). ( P Ph3I2C 12( C 0)Ru =C / SR RS' ( P Ph3 l2 C l2 (C 0)R u cI =C / \ 'CI 154 155 1 HSCH2CH2SH (PPh3)2C12(CO) Ru=C "I 'S 156 The cationic vinylidene complex 157 adds S-H across the double bond 37 Organosulfur and Organoselenium Organometallic Compounds of the vinylidene ligand to give a sulfhydryl ( R = H) or a methylthiocarbene ( R = Me) complex (158) (127).