Synthesis and structures of heterasumanenes having different heteroatom functionalities

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

Research output: Contribution to journalArticle

44 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 languageEnglish
Pages (from-to)672-675
Number of pages4
JournalTetrahedron Letters
Volume51
Issue number4
DOIs
Publication statusPublished - Jan 27 2010
Externally publishedYes

Fingerprint

Thiophenes
Carbon
dichlorodimethylsilane
butyllithium
dibenzothiophene
dichlorodimethylstannane

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis and structures of heterasumanenes having different heteroatom functionalities. / Saito, Masaichi; Tanikawa, Tomoharu; Tajima, Tomoyuki; Guo, Jing Dong; Nagase, Shigeru.

In: Tetrahedron Letters, Vol. 51, No. 4, 27.01.2010, p. 672-675.

Research output: Contribution to journalArticle

Saito, Masaichi ; Tanikawa, Tomoharu ; Tajima, Tomoyuki ; Guo, Jing Dong ; Nagase, Shigeru. / Synthesis and structures of heterasumanenes having different heteroatom functionalities. In: Tetrahedron Letters. 2010 ; Vol. 51, No. 4. pp. 672-675.
@article{e26b04f972d042fa84c1aa7b1be5e1f7,
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",
year = "2010",
month = "1",
day = "27",
doi = "10.1016/j.tetlet.2009.11.102",
language = "English",
volume = "51",
pages = "672--675",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "4",

}

TY - JOUR

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

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.

UR - http://www.scopus.com/inward/record.url?scp=72149116182&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=72149116182&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2009.11.102

DO - 10.1016/j.tetlet.2009.11.102

M3 - Article

VL - 51

SP - 672

EP - 675

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 4

ER -