Diacenaphtho[1,2-c:1′,2′-e]-1,2-dithiin: Synthesis, structure and reactivity

Richard D. Adams; Burjor Captain; Jack L. Smith

doi:10.1016/j.jorganchem.2003.09.031

Diacenaphtho[1,2-c:1′,2′-e]-1,2-dithiin: Synthesis, structure and reactivity

Richard D. Adams, Burjor Captain, Jack L. Smith

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

Diacenaphtho[1,2-c:1^′,2^′-e]-1,2-dithiin 2 was synthesized in 23% yield by the reaction of acenaphthylene with elemental sulfur at 120 °C. This reaction also afforded either diacenaphtho[1,2-b:1^′,2^′-d]thiophene 1 or diacenaphtho[1,2-b:1^′,2^′-e]- dihydro[e]-1,4-dithiin 3 depending on the reaction time. Compound 2 was desulfurized and converted to 1 under UV-vis irradiation in a benzene solution. Reaction of 2 with Pt(COD)₂ yielded the complex Pt(COD)(C₂₄H₁₂S₂) 4 (COD=1,5-cyclooctadiene) by insertion of a Pt(COD) group into the S-S bond of 2. When heated, 4 was desulfurized and converted to 1 by elimination of a (COD)PtS grouping. Compounds 1-4 were characterized crystallographically.

Original language	English (US)
Pages (from-to)	65-70
Number of pages	6
Journal	Journal of Organometallic Chemistry
Volume	689
Issue number	1
DOIs	https://doi.org/10.1016/j.jorganchem.2003.09.031
State	Published - Jan 5 2004
Externally published	Yes

Keywords

Diacenaphthodihydrodithiin
Diacenaphthodithiin
Diacenaphthothiophene
Platinum insertion

ASJC Scopus subject areas

Biochemistry
Inorganic Chemistry
Organic Chemistry
Physical and Theoretical Chemistry
Materials Chemistry

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title = "Diacenaphtho[1,2-c:1′,2′-e]-1,2-dithiin: Synthesis, structure and reactivity",

abstract = "Diacenaphtho[1,2-c:1′,2′-e]-1,2-dithiin 2 was synthesized in 23% yield by the reaction of acenaphthylene with elemental sulfur at 120 °C. This reaction also afforded either diacenaphtho[1,2-b:1′,2′-d]thiophene 1 or diacenaphtho[1,2-b:1′,2′-e]- dihydro[e]-1,4-dithiin 3 depending on the reaction time. Compound 2 was desulfurized and converted to 1 under UV-vis irradiation in a benzene solution. Reaction of 2 with Pt(COD)2 yielded the complex Pt(COD)(C24H12S2) 4 (COD=1,5-cyclooctadiene) by insertion of a Pt(COD) group into the S-S bond of 2. When heated, 4 was desulfurized and converted to 1 by elimination of a (COD)PtS grouping. Compounds 1-4 were characterized crystallographically.",

keywords = "Diacenaphthodihydrodithiin, Diacenaphthodithiin, Diacenaphthothiophene, Platinum insertion",

author = "Adams, {Richard D.} and Burjor Captain and Smith, {Jack L.}",

note = "Funding Information: This research was supported by a grant from the National Science Foundation, CHE-9909017. ",

year = "2004",

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doi = "10.1016/j.jorganchem.2003.09.031",

language = "English (US)",

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AU - Adams, Richard D.

AU - Captain, Burjor

AU - Smith, Jack L.

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PY - 2004/1/5

Y1 - 2004/1/5

N2 - Diacenaphtho[1,2-c:1′,2′-e]-1,2-dithiin 2 was synthesized in 23% yield by the reaction of acenaphthylene with elemental sulfur at 120 °C. This reaction also afforded either diacenaphtho[1,2-b:1′,2′-d]thiophene 1 or diacenaphtho[1,2-b:1′,2′-e]- dihydro[e]-1,4-dithiin 3 depending on the reaction time. Compound 2 was desulfurized and converted to 1 under UV-vis irradiation in a benzene solution. Reaction of 2 with Pt(COD)2 yielded the complex Pt(COD)(C24H12S2) 4 (COD=1,5-cyclooctadiene) by insertion of a Pt(COD) group into the S-S bond of 2. When heated, 4 was desulfurized and converted to 1 by elimination of a (COD)PtS grouping. Compounds 1-4 were characterized crystallographically.

AB - Diacenaphtho[1,2-c:1′,2′-e]-1,2-dithiin 2 was synthesized in 23% yield by the reaction of acenaphthylene with elemental sulfur at 120 °C. This reaction also afforded either diacenaphtho[1,2-b:1′,2′-d]thiophene 1 or diacenaphtho[1,2-b:1′,2′-e]- dihydro[e]-1,4-dithiin 3 depending on the reaction time. Compound 2 was desulfurized and converted to 1 under UV-vis irradiation in a benzene solution. Reaction of 2 with Pt(COD)2 yielded the complex Pt(COD)(C24H12S2) 4 (COD=1,5-cyclooctadiene) by insertion of a Pt(COD) group into the S-S bond of 2. When heated, 4 was desulfurized and converted to 1 by elimination of a (COD)PtS grouping. Compounds 1-4 were characterized crystallographically.

KW - Diacenaphthodihydrodithiin

KW - Diacenaphthodithiin

KW - Diacenaphthothiophene

KW - Platinum insertion

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Diacenaphtho[1,2-c:1′,2′-e]-1,2-dithiin: Synthesis, structure and reactivity

Abstract

Keywords

ASJC Scopus subject areas

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