β-Trichlorostannyl Ketones and Aldehydes. Preparation and Facile Amine-Induced Dehydrostannation Leading to α-Methylene Ketones and Aldehydes

Hiroyuki Nakahira; Ilhyong Ryu; Masanobu Ikebe; Yoshiaki Oku; Akiya Ogawa; Nobuaki Kambe; Noboru Sonoda; Shinji Murai

doi:10.1021/jo00027a008

β-Trichlorostannyl Ketones and Aldehydes. Preparation and Facile Amine-Induced Dehydrostannation Leading to α-Methylene Ketones and Aldehydes

Hiroyuki Nakahira, Ilhyong Ryu^*, Masanobu Ikebe, Yoshiaki Oku, Akiya Ogawa, Nobuaki Kambe, Noboru Sonoda, Shinji Murai

^*Corresponding author for this work

Department of Applied Chemistry

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

47 Scopus citations

Abstract

Ring-opening reactions of siloxycyclopropanes 1 with SnCl₄ take place under mild reaction conditions and site-selectively to give β-trichlorostannyl ketones and aldehydes 3 in high yields. The β-trichlorostannyl ketones and aldehydes thus obtained readily undergo base-induced dehydrotrichlorostannation at room temperature to give the corresponding α-methylene ketones and aldehydes 4. The reactions are quite general for amines, such as pyridine, triethylamine, N,N,N′,N′-tetramethylethylenediamine (TMEDA), and 1,4-diazabicyclo[2.2.2]octane (DABCO), and the yields are good to high. One-pot conversion from siloxycyclopropanes 1 to α-methylene ketones or aldehydes 4 by consecutive treatment of 1 with SnCl₄ and TMEDA is also successful. The ¹H NMR, ¹³C NMR, ¹¹⁹Sn NMR, and IR spectral properties of β-stannyl ketones and aldehydes are also reported.

Original language	English
Pages (from-to)	17-28
Number of pages	12
Journal	Journal of Organic Chemistry
Volume	57
Issue number	1
DOIs	https://doi.org/10.1021/jo00027a008
State	Published - 1 Jan 1992

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title = "β-Trichlorostannyl Ketones and Aldehydes. Preparation and Facile Amine-Induced Dehydrostannation Leading to α-Methylene Ketones and Aldehydes",

abstract = "Ring-opening reactions of siloxycyclopropanes 1 with SnCl4 take place under mild reaction conditions and site-selectively to give β-trichlorostannyl ketones and aldehydes 3 in high yields. The β-trichlorostannyl ketones and aldehydes thus obtained readily undergo base-induced dehydrotrichlorostannation at room temperature to give the corresponding α-methylene ketones and aldehydes 4. The reactions are quite general for amines, such as pyridine, triethylamine, N,N,N′,N′-tetramethylethylenediamine (TMEDA), and 1,4-diazabicyclo[2.2.2]octane (DABCO), and the yields are good to high. One-pot conversion from siloxycyclopropanes 1 to α-methylene ketones or aldehydes 4 by consecutive treatment of 1 with SnCl4 and TMEDA is also successful. The 1H NMR, 13C NMR, 119Sn NMR, and IR spectral properties of β-stannyl ketones and aldehydes are also reported.",

author = "Hiroyuki Nakahira and Ilhyong Ryu and Masanobu Ikebe and Yoshiaki Oku and Akiya Ogawa and Nobuaki Kambe and Noboru Sonoda and Shinji Murai",

year = "1992",

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doi = "10.1021/jo00027a008",

language = "English",

volume = "57",

pages = "17--28",

journal = "Journal of Organic Chemistry",

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publisher = "American Chemical Society",

number = "1",

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β-Trichlorostannyl Ketones and Aldehydes. Preparation and Facile Amine-Induced Dehydrostannation Leading to α-Methylene Ketones and Aldehydes. / Nakahira, Hiroyuki; Ryu, Ilhyong; Ikebe, Masanobu; Oku, Yoshiaki; Ogawa, Akiya; Kambe, Nobuaki; Sonoda, Noboru; Murai, Shinji.

In: Journal of Organic Chemistry, Vol. 57, No. 1, 01.01.1992, p. 17-28.

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

TY - JOUR

T1 - β-Trichlorostannyl Ketones and Aldehydes. Preparation and Facile Amine-Induced Dehydrostannation Leading to α-Methylene Ketones and Aldehydes

AU - Nakahira, Hiroyuki

AU - Ryu, Ilhyong

AU - Ikebe, Masanobu

AU - Oku, Yoshiaki

AU - Ogawa, Akiya

AU - Kambe, Nobuaki

AU - Sonoda, Noboru

AU - Murai, Shinji

PY - 1992/1/1

Y1 - 1992/1/1

N2 - Ring-opening reactions of siloxycyclopropanes 1 with SnCl4 take place under mild reaction conditions and site-selectively to give β-trichlorostannyl ketones and aldehydes 3 in high yields. The β-trichlorostannyl ketones and aldehydes thus obtained readily undergo base-induced dehydrotrichlorostannation at room temperature to give the corresponding α-methylene ketones and aldehydes 4. The reactions are quite general for amines, such as pyridine, triethylamine, N,N,N′,N′-tetramethylethylenediamine (TMEDA), and 1,4-diazabicyclo[2.2.2]octane (DABCO), and the yields are good to high. One-pot conversion from siloxycyclopropanes 1 to α-methylene ketones or aldehydes 4 by consecutive treatment of 1 with SnCl4 and TMEDA is also successful. The 1H NMR, 13C NMR, 119Sn NMR, and IR spectral properties of β-stannyl ketones and aldehydes are also reported.

AB - Ring-opening reactions of siloxycyclopropanes 1 with SnCl4 take place under mild reaction conditions and site-selectively to give β-trichlorostannyl ketones and aldehydes 3 in high yields. The β-trichlorostannyl ketones and aldehydes thus obtained readily undergo base-induced dehydrotrichlorostannation at room temperature to give the corresponding α-methylene ketones and aldehydes 4. The reactions are quite general for amines, such as pyridine, triethylamine, N,N,N′,N′-tetramethylethylenediamine (TMEDA), and 1,4-diazabicyclo[2.2.2]octane (DABCO), and the yields are good to high. One-pot conversion from siloxycyclopropanes 1 to α-methylene ketones or aldehydes 4 by consecutive treatment of 1 with SnCl4 and TMEDA is also successful. The 1H NMR, 13C NMR, 119Sn NMR, and IR spectral properties of β-stannyl ketones and aldehydes are also reported.

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β-Trichlorostannyl Ketones and Aldehydes. Preparation and Facile Amine-Induced Dehydrostannation Leading to α-Methylene Ketones and Aldehydes

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