A new synthetic route for silacyclopropanes

Reactions of a bromosilylenoid with olefins

Hyeon Mo Cho, Kyongjin Bok, Seo Hyeon Park, Young Mook Lim, Myong Euy Lee, Moon-Gun Choi, Kang Mun Lee

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Stable 1-bromo-1-silacyclopropanes were synthesized in high yields from the reaction of the stable bromotrisylsilylenoid 1 (trisyl = C(SiMe 3) 3) with olefins such as styrene, trimethylvinylsilane, triethylvinylsilane, and dimethylphenylvinylsilane, a new synthetic route for silacyclopropanes. The structure of bromosilacyclopropane 5 was confirmed by X-ray analysis. In the presence of excess MeOH the phenyl-substituted bromosilacyclopropane 2 underwent regioselective ring opening to give the corresponding product 6. In contrast, the reaction of silyl-substituted bromosilacyclopropane 5 with MeOH gave only the product of nucleophilic substitution at the silicon atom, 1-methoxy-1-silacyclopropane 7, without any ring opening. Furthermore, the bromosilacyclopropane 2 extruded bromosilylene 8 through a thermal cycloreversion reaction.

Original languageEnglish
Pages (from-to)5227-5230
Number of pages4
JournalOrganometallics
Volume31
Issue number15
DOIs
Publication statusPublished - 2012 Aug 13

Fingerprint

Styrene
X ray analysis
Alkenes
Silicon
alkenes
Substitution reactions
routes
Atoms
rings
products
styrenes
substitutes
silicon
atoms
Hot Temperature
x rays

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Cho, H. M., Bok, K., Park, S. H., Lim, Y. M., Lee, M. E., Choi, M-G., & Lee, K. M. (2012). A new synthetic route for silacyclopropanes: Reactions of a bromosilylenoid with olefins. Organometallics, 31(15), 5227-5230. https://doi.org/10.1021/om3005349
Cho, Hyeon Mo ; Bok, Kyongjin ; Park, Seo Hyeon ; Lim, Young Mook ; Lee, Myong Euy ; Choi, Moon-Gun ; Lee, Kang Mun. / A new synthetic route for silacyclopropanes : Reactions of a bromosilylenoid with olefins. In: Organometallics. 2012 ; Vol. 31, No. 15. pp. 5227-5230.
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abstract = "Stable 1-bromo-1-silacyclopropanes were synthesized in high yields from the reaction of the stable bromotrisylsilylenoid 1 (trisyl = C(SiMe 3) 3) with olefins such as styrene, trimethylvinylsilane, triethylvinylsilane, and dimethylphenylvinylsilane, a new synthetic route for silacyclopropanes. The structure of bromosilacyclopropane 5 was confirmed by X-ray analysis. In the presence of excess MeOH the phenyl-substituted bromosilacyclopropane 2 underwent regioselective ring opening to give the corresponding product 6. In contrast, the reaction of silyl-substituted bromosilacyclopropane 5 with MeOH gave only the product of nucleophilic substitution at the silicon atom, 1-methoxy-1-silacyclopropane 7, without any ring opening. Furthermore, the bromosilacyclopropane 2 extruded bromosilylene 8 through a thermal cycloreversion reaction.",
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Cho, HM, Bok, K, Park, SH, Lim, YM, Lee, ME, Choi, M-G & Lee, KM 2012, 'A new synthetic route for silacyclopropanes: Reactions of a bromosilylenoid with olefins', Organometallics, vol. 31, no. 15, pp. 5227-5230. https://doi.org/10.1021/om3005349

A new synthetic route for silacyclopropanes : Reactions of a bromosilylenoid with olefins. / Cho, Hyeon Mo; Bok, Kyongjin; Park, Seo Hyeon; Lim, Young Mook; Lee, Myong Euy; Choi, Moon-Gun; Lee, Kang Mun.

In: Organometallics, Vol. 31, No. 15, 13.08.2012, p. 5227-5230.

Research output: Contribution to journalArticle

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AU - Lee, Myong Euy

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AU - Lee, Kang Mun

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N2 - Stable 1-bromo-1-silacyclopropanes were synthesized in high yields from the reaction of the stable bromotrisylsilylenoid 1 (trisyl = C(SiMe 3) 3) with olefins such as styrene, trimethylvinylsilane, triethylvinylsilane, and dimethylphenylvinylsilane, a new synthetic route for silacyclopropanes. The structure of bromosilacyclopropane 5 was confirmed by X-ray analysis. In the presence of excess MeOH the phenyl-substituted bromosilacyclopropane 2 underwent regioselective ring opening to give the corresponding product 6. In contrast, the reaction of silyl-substituted bromosilacyclopropane 5 with MeOH gave only the product of nucleophilic substitution at the silicon atom, 1-methoxy-1-silacyclopropane 7, without any ring opening. Furthermore, the bromosilacyclopropane 2 extruded bromosilylene 8 through a thermal cycloreversion reaction.

AB - Stable 1-bromo-1-silacyclopropanes were synthesized in high yields from the reaction of the stable bromotrisylsilylenoid 1 (trisyl = C(SiMe 3) 3) with olefins such as styrene, trimethylvinylsilane, triethylvinylsilane, and dimethylphenylvinylsilane, a new synthetic route for silacyclopropanes. The structure of bromosilacyclopropane 5 was confirmed by X-ray analysis. In the presence of excess MeOH the phenyl-substituted bromosilacyclopropane 2 underwent regioselective ring opening to give the corresponding product 6. In contrast, the reaction of silyl-substituted bromosilacyclopropane 5 with MeOH gave only the product of nucleophilic substitution at the silicon atom, 1-methoxy-1-silacyclopropane 7, without any ring opening. Furthermore, the bromosilacyclopropane 2 extruded bromosilylene 8 through a thermal cycloreversion reaction.

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