A novel cyclopropanation

Tracy Matthew Bostick; Sean D. Christie; Terrence Joseph Connolly; Steven Copp; Richard Francis Langler; Darren Leonard Reid; Michael Zaworotko

doi:10.1071/ch9960243

A novel cyclopropanation

Tracy Matthew Bostick
, Sean D. Christie
, Terrence Joseph Connolly
, Steven Copp
, Richard Francis Langler
, Darren Leonard Reid
, Michael Zaworotko

Mount Allison University
Saint Mary's University Halifax

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

Abstract

Reaction between benzaldehyde and methyl α-benzylsulfonylacetate furnishes methyl (E)-α-benzylsulfonyl-β-phenylacrylate as the exclusive Knoevenagel adduct. The related condensations between α-benzylsulfonylacetonitrile and paraformaldehyde furnish trans-1-benzylsulfonyl-2-phenylcyclopropane-1-carbonitrile in modest yields. These product structures are established by X-ray crystallographic analysis. Phenylsulfene is ruled out as an intermediate in the formation of the cyclopropane.

Original language	English
Pages (from-to)	243-247
Number of pages	5
Journal	Australian Journal of Chemistry
Volume	49
Issue number	2
DOIs	https://doi.org/10.1071/ch9960243
Publication status	Published - 1996
Externally published	Yes

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title = "A novel cyclopropanation",

abstract = "Reaction between benzaldehyde and methyl α-benzylsulfonylacetate furnishes methyl (E)-α-benzylsulfonyl-β-phenylacrylate as the exclusive Knoevenagel adduct. The related condensations between α-benzylsulfonylacetonitrile and paraformaldehyde furnish trans-1-benzylsulfonyl-2-phenylcyclopropane-1-carbonitrile in modest yields. These product structures are established by X-ray crystallographic analysis. Phenylsulfene is ruled out as an intermediate in the formation of the cyclopropane.",

author = "Bostick, \{Tracy Matthew\} and Christie, \{Sean D.\} and Connolly, \{Terrence Joseph\} and Steven Copp and Langler, \{Richard Francis\} and Reid, \{Darren Leonard\} and Michael Zaworotko",

year = "1996",

doi = "10.1071/ch9960243",

language = "English",

volume = "49",

pages = "243--247",

journal = "Australian Journal of Chemistry",

issn = "0004-9425",

number = "2",

}

TY - JOUR

T1 - A novel cyclopropanation

AU - Bostick, Tracy Matthew

AU - Christie, Sean D.

AU - Connolly, Terrence Joseph

AU - Copp, Steven

AU - Langler, Richard Francis

AU - Reid, Darren Leonard

AU - Zaworotko, Michael

PY - 1996

Y1 - 1996

N2 - Reaction between benzaldehyde and methyl α-benzylsulfonylacetate furnishes methyl (E)-α-benzylsulfonyl-β-phenylacrylate as the exclusive Knoevenagel adduct. The related condensations between α-benzylsulfonylacetonitrile and paraformaldehyde furnish trans-1-benzylsulfonyl-2-phenylcyclopropane-1-carbonitrile in modest yields. These product structures are established by X-ray crystallographic analysis. Phenylsulfene is ruled out as an intermediate in the formation of the cyclopropane.

AB - Reaction between benzaldehyde and methyl α-benzylsulfonylacetate furnishes methyl (E)-α-benzylsulfonyl-β-phenylacrylate as the exclusive Knoevenagel adduct. The related condensations between α-benzylsulfonylacetonitrile and paraformaldehyde furnish trans-1-benzylsulfonyl-2-phenylcyclopropane-1-carbonitrile in modest yields. These product structures are established by X-ray crystallographic analysis. Phenylsulfene is ruled out as an intermediate in the formation of the cyclopropane.

UR - https://www.scopus.com/pages/publications/0010714785

U2 - 10.1071/ch9960243

DO - 10.1071/ch9960243

M3 - Article

AN - SCOPUS:0010714785

SN - 0004-9425

VL - 49

SP - 243

EP - 247

JO - Australian Journal of Chemistry

JF - Australian Journal of Chemistry

IS - 2

ER -

A novel cyclopropanation

Abstract

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