An Unusual Simmons-Smith Reaction Affording Noncyclopropyl Compounds. New Route to 2-Methylenecycloalkanols from Silyl Alkenyl Ethers

Shinji Murai; Tomoyuki Aya; Tsumoru Renge; Ilhyong Ryu; Noboru Sonoda

doi:10.1021/jo00920a032

An Unusual Simmons-Smith Reaction Affording Noncyclopropyl Compounds. New Route to 2-Methylenecycloalkanols from Silyl Alkenyl Ethers

Shinji Murai^*, Tomoyuki Aya, Tsumoru Renge, Ilhyong Ryu, Noboru Sonoda

^*Corresponding author for this work

Department of Applied Chemistry

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

32 Scopus citations

Abstract

Reaction of silyl cycloalkenyl ethers under a certain Simmons-Smith reaction conditions gives silyl ethers of 2-methylenecycloalkanols, and these noncyclopropyl products have been shown to arise by the isomerization of initially produced silyl cyclopropyl ethers with zinc iodide which is formed during the course of Simmons-Smith reaction.

Original language	English
Pages (from-to)	858-859
Number of pages	2
Journal	Journal of Organic Chemistry
Volume	39
Issue number	6
DOIs	https://doi.org/10.1021/jo00920a032
State	Published - 1 Mar 1974

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title = "An Unusual Simmons-Smith Reaction Affording Noncyclopropyl Compounds. New Route to 2-Methylenecycloalkanols from Silyl Alkenyl Ethers",

abstract = "Reaction of silyl cycloalkenyl ethers under a certain Simmons-Smith reaction conditions gives silyl ethers of 2-methylenecycloalkanols, and these noncyclopropyl products have been shown to arise by the isomerization of initially produced silyl cyclopropyl ethers with zinc iodide which is formed during the course of Simmons-Smith reaction.",

author = "Shinji Murai and Tomoyuki Aya and Tsumoru Renge and Ilhyong Ryu and Noboru Sonoda",

year = "1974",

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journal = "Journal of Organic Chemistry",

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T1 - An Unusual Simmons-Smith Reaction Affording Noncyclopropyl Compounds. New Route to 2-Methylenecycloalkanols from Silyl Alkenyl Ethers

AU - Murai, Shinji

AU - Aya, Tomoyuki

AU - Renge, Tsumoru

AU - Ryu, Ilhyong

AU - Sonoda, Noboru

PY - 1974/3/1

Y1 - 1974/3/1

N2 - Reaction of silyl cycloalkenyl ethers under a certain Simmons-Smith reaction conditions gives silyl ethers of 2-methylenecycloalkanols, and these noncyclopropyl products have been shown to arise by the isomerization of initially produced silyl cyclopropyl ethers with zinc iodide which is formed during the course of Simmons-Smith reaction.

AB - Reaction of silyl cycloalkenyl ethers under a certain Simmons-Smith reaction conditions gives silyl ethers of 2-methylenecycloalkanols, and these noncyclopropyl products have been shown to arise by the isomerization of initially produced silyl cyclopropyl ethers with zinc iodide which is formed during the course of Simmons-Smith reaction.

UR - http://www.scopus.com/inward/record.url?scp=0000553317&partnerID=8YFLogxK

U2 - 10.1021/jo00920a032

DO - 10.1021/jo00920a032

M3 - Letter

AN - SCOPUS:0000553317

SN - 0022-3263

VL - 39

SP - 858

EP - 859

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 6

ER -

An Unusual Simmons-Smith Reaction Affording Noncyclopropyl Compounds. New Route to 2-Methylenecycloalkanols from Silyl Alkenyl Ethers

Abstract

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