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Please login to access the full content or check if you have access via24.4.3.5.4.1.4 Method 4: Hydroalkoxylation and Hydrothiolation Reactions
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Ulfkjær, A.; Pittelkow, M., Science of Synthesis Knowledge Updates, (2018) 1, 196.
A series of multifunctional 1-(vinylsulfanyl)alk-1-ynes 139 containing a ferrocenyl group and a vinyl sulfide or ether functionality can be prepared from ferrocenyl-substituted diethynyl sulfide 40 (Scheme 106).[28] The hydroalkoxylation and hydrothiolation reactions are regioselective and exclusively yield the Z-isomers resulting from anti-Markovnikov addition. While the reaction with alcohols always gives the monohydroalkoxylation products, the reaction with thiols gives monohydrothiolation products when 5 equivalents of thiol is used, but dihydrothiolation products when a larger excess of thiol (20 equiv) is used (see Section 24.4.3.5.2.2.2)
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| M8 | M | Meeee ee M8MM | Meeeeee | Meee | Meeee (%) | Mee |
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| Me | M | –e | –e | 88 °M | 88 | [88] |
| Me | M | –e | –e | 88 °M | 88 | [88] |
| Me | M | 8 | MMM | ee | 88 | [88] |
| M8M8 | M | 8 | MMM | ee | 88e | [88] |
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References
| [28] | Meeeeee, M.; Meeeáeeee, M.; Meeeee, Á.; Meeeíe, M.; Meeee, M. M., M. Meeeeeeee. Meee., (8888) 888, 888. |
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