Synthesis and structures of heterasumanenes having different heteroatom functionalities

Masaichi Saito; Tomoharu Tanikawa; Tomoyuki Tajima; Jing Dong Guo; Shigeru Nagase

doi:10.1016/j.tetlet.2009.11.102

Synthesis and structures of heterasumanenes having different heteroatom functionalities

Masaichi Saito, Tomoharu Tanikawa, Tomoyuki Tajima, Jing Dong Guo, Shigeru Nagase

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

61 Citations (Scopus)

Abstract

After the protection of two α-carbons of the dibenzothiophene moiety in triphenylenothiophene 1 by trimethylsilyl groups, the resulting compound 4 reacted with butyllithium followed by dichlorodimethylsilane to afford 10H-silolo[2′,3′,4′,5′:4,5]triphenyleno[1,12-bcd]thiophene 8, which reacted with butyllithium followed by dichlorodimethylsilane to afford novel heterasumanene 11. Using dichlorodimethylstannane instead of dichlorodimethylsilane afforded heterasumanene 12, which is the first example of a heterasumanene having three different heteroatom functionalities.

Original language	English
Pages (from-to)	672-675
Number of pages	4
Journal	Tetrahedron Letters
Volume	51
Issue number	4
DOIs	https://doi.org/10.1016/j.tetlet.2009.11.102
Publication status	Published - Jan 27 2010
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2009.11.102

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title = "Synthesis and structures of heterasumanenes having different heteroatom functionalities",

abstract = "After the protection of two α-carbons of the dibenzothiophene moiety in triphenylenothiophene 1 by trimethylsilyl groups, the resulting compound 4 reacted with butyllithium followed by dichlorodimethylsilane to afford 10H-silolo[2′,3′,4′,5′:4,5]triphenyleno[1,12-bcd]thiophene 8, which reacted with butyllithium followed by dichlorodimethylsilane to afford novel heterasumanene 11. Using dichlorodimethylstannane instead of dichlorodimethylsilane afforded heterasumanene 12, which is the first example of a heterasumanene having three different heteroatom functionalities.",

author = "Masaichi Saito and Tomoharu Tanikawa and Tomoyuki Tajima and Guo, {Jing Dong} and Shigeru Nagase",

note = "Funding Information: This work was partially supported by the Nanotechnology Support Project from the Ministry of Education, Culture, Sports, Science, and Technology of Japan. M.S. acknowledges a prize for his research proposal and a grant from Konica Minolta Technology Center, Inc. and JGC-S Scholarship Foundation, respectively. ",

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T1 - Synthesis and structures of heterasumanenes having different heteroatom functionalities

AU - Saito, Masaichi

AU - Tanikawa, Tomoharu

AU - Tajima, Tomoyuki

AU - Guo, Jing Dong

AU - Nagase, Shigeru

N1 - Funding Information: This work was partially supported by the Nanotechnology Support Project from the Ministry of Education, Culture, Sports, Science, and Technology of Japan. M.S. acknowledges a prize for his research proposal and a grant from Konica Minolta Technology Center, Inc. and JGC-S Scholarship Foundation, respectively.

PY - 2010/1/27

Y1 - 2010/1/27

N2 - After the protection of two α-carbons of the dibenzothiophene moiety in triphenylenothiophene 1 by trimethylsilyl groups, the resulting compound 4 reacted with butyllithium followed by dichlorodimethylsilane to afford 10H-silolo[2′,3′,4′,5′:4,5]triphenyleno[1,12-bcd]thiophene 8, which reacted with butyllithium followed by dichlorodimethylsilane to afford novel heterasumanene 11. Using dichlorodimethylstannane instead of dichlorodimethylsilane afforded heterasumanene 12, which is the first example of a heterasumanene having three different heteroatom functionalities.

AB - After the protection of two α-carbons of the dibenzothiophene moiety in triphenylenothiophene 1 by trimethylsilyl groups, the resulting compound 4 reacted with butyllithium followed by dichlorodimethylsilane to afford 10H-silolo[2′,3′,4′,5′:4,5]triphenyleno[1,12-bcd]thiophene 8, which reacted with butyllithium followed by dichlorodimethylsilane to afford novel heterasumanene 11. Using dichlorodimethylstannane instead of dichlorodimethylsilane afforded heterasumanene 12, which is the first example of a heterasumanene having three different heteroatom functionalities.

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Synthesis and structures of heterasumanenes having different heteroatom functionalities

Abstract

ASJC Scopus subject areas

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