Regioselective cycloaddition reaction of alkene molecules with the asymmetric dimer on Si(100)c(4x2)

Kazuhiro Oguchi; Masashi Nagao; Hirobumi Umeyama; Tetsuo Katayama; Yoshiyuki Yamashita; Kozo Mukai; Jun Yoshinobu; Kazuto Akagi; Shinji Tsuneyuki

doi:10.1021/ja066285i

Regioselective cycloaddition reaction of alkene molecules with the asymmetric dimer on Si(100)c(4x2)

Kazuhiro Oguchi, Masashi Nagao, Hirobumi Umeyama, Tetsuo Katayama, Yoshiyuki Yamashita, Kozo Mukai, Jun Yoshinobu, Kazuto Akagi, Shinji Tsuneyuki

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

5 Citations (Scopus)

Abstract

We investigated the adsorption states of 2-methylpropene and propene on Si(100)c(4x2) using low-temperature scanning tunneling microscopy. We have found that regioselective cycloaddition reactions (di-σ bond formation) occur between the asymmetric alkene molecules and the asymmetric dimers on Si-(100)c(4x2). First-principles calculations have elucidated that the regioselectivity is closely related to the structures of precursor species and these precursor species have carbocation-like features. Thus, we conclude that Markovnikov's rule is applicable for the cycloaddition of asymmetric alkene with the asymmetric dimer on Si(100)c(4x2).

Original language	English
Pages (from-to)	1242-1245
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	129
Issue number	5
DOIs	https://doi.org/10.1021/ja066285i
Publication status	Published - 2007 Feb 7
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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Regioselective cycloaddition reaction of alkene molecules with the asymmetric dimer on Si(100)c(4x2). / Oguchi, Kazuhiro; Nagao, Masashi; Umeyama, Hirobumi; Katayama, Tetsuo; Yamashita, Yoshiyuki; Mukai, Kozo; Yoshinobu, Jun; Akagi, Kazuto; Tsuneyuki, Shinji.

In: Journal of the American Chemical Society, Vol. 129, No. 5, 07.02.2007, p. 1242-1245.

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

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abstract = "We investigated the adsorption states of 2-methylpropene and propene on Si(100)c(4x2) using low-temperature scanning tunneling microscopy. We have found that regioselective cycloaddition reactions (di-σ bond formation) occur between the asymmetric alkene molecules and the asymmetric dimers on Si-(100)c(4x2). First-principles calculations have elucidated that the regioselectivity is closely related to the structures of precursor species and these precursor species have carbocation-like features. Thus, we conclude that Markovnikov's rule is applicable for the cycloaddition of asymmetric alkene with the asymmetric dimer on Si(100)c(4x2).",

author = "Kazuhiro Oguchi and Masashi Nagao and Hirobumi Umeyama and Tetsuo Katayama and Yoshiyuki Yamashita and Kozo Mukai and Jun Yoshinobu and Kazuto Akagi and Shinji Tsuneyuki",

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T1 - Regioselective cycloaddition reaction of alkene molecules with the asymmetric dimer on Si(100)c(4x2)

AU - Oguchi, Kazuhiro

AU - Nagao, Masashi

AU - Umeyama, Hirobumi

AU - Katayama, Tetsuo

AU - Yamashita, Yoshiyuki

AU - Mukai, Kozo

AU - Yoshinobu, Jun

AU - Akagi, Kazuto

AU - Tsuneyuki, Shinji

PY - 2007/2/7

Y1 - 2007/2/7

N2 - We investigated the adsorption states of 2-methylpropene and propene on Si(100)c(4x2) using low-temperature scanning tunneling microscopy. We have found that regioselective cycloaddition reactions (di-σ bond formation) occur between the asymmetric alkene molecules and the asymmetric dimers on Si-(100)c(4x2). First-principles calculations have elucidated that the regioselectivity is closely related to the structures of precursor species and these precursor species have carbocation-like features. Thus, we conclude that Markovnikov's rule is applicable for the cycloaddition of asymmetric alkene with the asymmetric dimer on Si(100)c(4x2).

AB - We investigated the adsorption states of 2-methylpropene and propene on Si(100)c(4x2) using low-temperature scanning tunneling microscopy. We have found that regioselective cycloaddition reactions (di-σ bond formation) occur between the asymmetric alkene molecules and the asymmetric dimers on Si-(100)c(4x2). First-principles calculations have elucidated that the regioselectivity is closely related to the structures of precursor species and these precursor species have carbocation-like features. Thus, we conclude that Markovnikov's rule is applicable for the cycloaddition of asymmetric alkene with the asymmetric dimer on Si(100)c(4x2).

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Regioselective cycloaddition reaction of alkene molecules with the asymmetric dimer on Si(100)c(4x2)

Abstract

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