Novel reactions of steric encumbered 1,4-dilithio-1,3-butadiene with group 14 electrophiles: Formation and structure of stable dihydroxygermole

Masaichi Saito; Michio Nakamura; Tomoyuki Tajima

doi:10.3987/COM-08-11547

Novel reactions of steric encumbered 1,4-dilithio-1,3-butadiene with group 14 electrophiles: Formation and structure of stable dihydroxygermole

Masaichi Saito, Michio Nakamura, Tomoyuki Tajima

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

3 Citations (Scopus)

Abstract

Reactions of 1,4-dilithio-1,3-butadiene 1 having bulky silyl ligands at the 1,4-positions with group 14 electrophiles were examined. Reactions of 1,4-dilithio-1,3-butadiene 1 with tetraethoxygermane gave diethoxygermole 5, which was hydrolyzed to give stable dihydroxygermole 16. The X-ray diffraction analysis of dihydroxygermole 16 revealed intermolecular hydrogen bonds. The reaction of 1 with stannous chloride was also examined.

Original language	English
Pages (from-to)	657-668
Number of pages	12
Journal	Heterocycles
Volume	78
Issue number	3
DOIs	https://doi.org/10.3987/COM-08-11547
Publication status	Published - Mar 1 2009
Externally published	Yes

Keywords

1,4-Dilithio-1,3-butadiene
Diethoxygermole
Dihydroxygermole
Group 14 Electrophile

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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abstract = "Reactions of 1,4-dilithio-1,3-butadiene 1 having bulky silyl ligands at the 1,4-positions with group 14 electrophiles were examined. Reactions of 1,4-dilithio-1,3-butadiene 1 with tetraethoxygermane gave diethoxygermole 5, which was hydrolyzed to give stable dihydroxygermole 16. The X-ray diffraction analysis of dihydroxygermole 16 revealed intermolecular hydrogen bonds. The reaction of 1 with stannous chloride was also examined.",

keywords = "1,4-Dilithio-1,3-butadiene, Diethoxygermole, Dihydroxygermole, Group 14 Electrophile",

author = "Masaichi Saito and Michio Nakamura and Tomoyuki Tajima",

year = "2009",

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doi = "10.3987/COM-08-11547",

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T1 - Novel reactions of steric encumbered 1,4-dilithio-1,3-butadiene with group 14 electrophiles

T2 - Formation and structure of stable dihydroxygermole

AU - Saito, Masaichi

AU - Nakamura, Michio

AU - Tajima, Tomoyuki

PY - 2009/3/1

Y1 - 2009/3/1

N2 - Reactions of 1,4-dilithio-1,3-butadiene 1 having bulky silyl ligands at the 1,4-positions with group 14 electrophiles were examined. Reactions of 1,4-dilithio-1,3-butadiene 1 with tetraethoxygermane gave diethoxygermole 5, which was hydrolyzed to give stable dihydroxygermole 16. The X-ray diffraction analysis of dihydroxygermole 16 revealed intermolecular hydrogen bonds. The reaction of 1 with stannous chloride was also examined.

AB - Reactions of 1,4-dilithio-1,3-butadiene 1 having bulky silyl ligands at the 1,4-positions with group 14 electrophiles were examined. Reactions of 1,4-dilithio-1,3-butadiene 1 with tetraethoxygermane gave diethoxygermole 5, which was hydrolyzed to give stable dihydroxygermole 16. The X-ray diffraction analysis of dihydroxygermole 16 revealed intermolecular hydrogen bonds. The reaction of 1 with stannous chloride was also examined.

KW - 1,4-Dilithio-1,3-butadiene

KW - Diethoxygermole

KW - Dihydroxygermole

KW - Group 14 Electrophile

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Novel reactions of steric encumbered 1,4-dilithio-1,3-butadiene with group 14 electrophiles: Formation and structure of stable dihydroxygermole

Abstract

Keywords

ASJC Scopus subject areas

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