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Lah, Myoung Soo
Nanoporous Materials Lab
Research Interests
  • Metal-Organic Frameworks (MOFs)

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Manganese thiophene tricarbonyl complexes: Nucleophilic addition to sulfur and synthesis of thiophenium salts

Cited 13 times inthomson ciCited 11 times inthomson ci
Title
Manganese thiophene tricarbonyl complexes: Nucleophilic addition to sulfur and synthesis of thiophenium salts
Author
Lee, SSLee, TYChoi, DSLee, JSChung, YKLee, SWLah, Myoung Soo
Keywords
MOLECULAR-STRUCTURE; ELECTROPHILIC REACTIVITY; BASE HYDROLYSIS; X-RAY; CATIONS; DICARBONYLNITROSYL(CYCLOHEXADIENYL)MANGANESE; HYDRODESULFURIZATION; PERCHLORATE; REAGENTS; LIGANDS
Issue Date
199704
Publisher
AMER CHEMICAL SOC
Citation
ORGANOMETALLICS, v.16, no.8, pp.1749 - 1756
Abstract
New thiophene manganese derivatives, [(2-R1-C4H3S)Mn(CO)3]+ 1(sil) (R1 = Si(OCH2-CH2)3N) and 1(Mn) (R1 = (C6H6)Mn(CO)3), have been synthesized and their reaction with nucleophiles studied. Except for the Grignard reagent, nucleophiles (Nu- = H-, -CN, -P(O)(OR)2 (R = Me, Ph)) usually attack the C5 position. Grignard reagents attack the sulfur atom to yield manganese S-R-thiophene carbonyls 3. To compare the reactivities of 1(sil) and 1(Mn) with that of (thiophene)Mn(CO)3 + with respect to Grignard reagent addition, the known compounds [(thiophene)Mn(CO)3]+ (thiophene = thiophene, 2-methylthiophene, 2,5-dimethylthiophene) have been synthesized and their reaction with Grignard reagents studied. In all cases, S-R-thiophene manganese carbonyls 3 were obtained as a sole product. Refluxing 3 (R = Ph, p-tolyl, 2-thienyl) with Me3NO in benzene yielded diaryl sulfide. Treatment of 3 with NOBF4 in CH2Cl2 led to S-R-thiophenium-manganese dicarbonyl nitrosyl cations 4. Photolysis of 4 in acetone gave rise to S-R-thiophenium 5 in high yields. The molecular structures of [{2-exo-P(O)(OMe)2η4-C4H 3S}Mn(CO)3] (2(sil,P(O)(OMe)2)), [S-Ph-η4-2-{(η5-C6H 6)Mn(CO)3}SC4H3]Mn(CO)3 (3(Mn,Ph)), and [p-CH3C6H5-S-2-CH3C 4H3] (5(Me,p-tolyl)) have been determined by X-ray studies.
URI
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DOI
http://dx.doi.org/10.1021/om970031b
ISSN
0276-7333
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