Preparation and chemistry of some 1-iodo-1-phenylpropenes

J. R. Campbell; A. Pross; S. Sternhell

doi:10.1071/CH9711425

Preparation and chemistry of some 1-iodo-1-phenylpropenes

J. R. Campbell
, A. Pross
, S. Sternhell

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

13 Scopus citations

Abstract

The oxidation of eight aryl alkyl hydrazones with iodine in the presence of triethylamine gave mixtures of 1-iodo-1-arylpropenes and ketones in yields of 36-73% and 19-43% respectively. Further evidence is presented in favour of an iodocarbonium ion intermediate for this reaction. Aspects of the photochemistry of 1-iodo-1-arylpropenes and their reaction with naphthylsodium are reported. The product distribution of the naphthylsodium reactions is consistent with an intermediate sp²-hybridized ("bent") 1-arylpropenyl radical.

Original language	English
Pages (from-to)	1425-1436
Number of pages	12
Journal	Australian Journal of Chemistry
Volume	24
Issue number	7
DOIs	https://doi.org/10.1071/CH9711425
State	Published - 1 Jan 1971
Externally published	Yes

ASJC Scopus subject areas

General Chemistry

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10.1071/CH9711425

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@article{10dbc77b83fd46bcacda952c692605e1,

title = "Preparation and chemistry of some 1-iodo-1-phenylpropenes",

abstract = "The oxidation of eight aryl alkyl hydrazones with iodine in the presence of triethylamine gave mixtures of 1-iodo-1-arylpropenes and ketones in yields of 36-73\% and 19-43\% respectively. Further evidence is presented in favour of an iodocarbonium ion intermediate for this reaction. Aspects of the photochemistry of 1-iodo-1-arylpropenes and their reaction with naphthylsodium are reported. The product distribution of the naphthylsodium reactions is consistent with an intermediate sp2-hybridized ({"}bent{"}) 1-arylpropenyl radical.",

author = "Campbell, \{J. R.\} and A. Pross and S. Sternhell",

note = "Funding Information: One of us (J.R.C.) wishes to acknowledge a Postdoctoral Scholarship from the National Research Council of Canada. This work was supported by ARGC Grant No. C65115567.",

year = "1971",

month = jan,

day = "1",

doi = "10.1071/CH9711425",

language = "English",

volume = "24",

pages = "1425--1436",

journal = "Australian Journal of Chemistry",

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T1 - Preparation and chemistry of some 1-iodo-1-phenylpropenes

AU - Campbell, J. R.

AU - Pross, A.

AU - Sternhell, S.

N1 - Funding Information: One of us (J.R.C.) wishes to acknowledge a Postdoctoral Scholarship from the National Research Council of Canada. This work was supported by ARGC Grant No. C65115567.

PY - 1971/1/1

Y1 - 1971/1/1

N2 - The oxidation of eight aryl alkyl hydrazones with iodine in the presence of triethylamine gave mixtures of 1-iodo-1-arylpropenes and ketones in yields of 36-73% and 19-43% respectively. Further evidence is presented in favour of an iodocarbonium ion intermediate for this reaction. Aspects of the photochemistry of 1-iodo-1-arylpropenes and their reaction with naphthylsodium are reported. The product distribution of the naphthylsodium reactions is consistent with an intermediate sp2-hybridized ("bent") 1-arylpropenyl radical.

AB - The oxidation of eight aryl alkyl hydrazones with iodine in the presence of triethylamine gave mixtures of 1-iodo-1-arylpropenes and ketones in yields of 36-73% and 19-43% respectively. Further evidence is presented in favour of an iodocarbonium ion intermediate for this reaction. Aspects of the photochemistry of 1-iodo-1-arylpropenes and their reaction with naphthylsodium are reported. The product distribution of the naphthylsodium reactions is consistent with an intermediate sp2-hybridized ("bent") 1-arylpropenyl radical.

UR - https://www.scopus.com/pages/publications/33947288689

U2 - 10.1071/CH9711425

DO - 10.1071/CH9711425

M3 - Article

AN - SCOPUS:33947288689

SN - 0004-9425

VL - 24

SP - 1425

EP - 1436

JO - Australian Journal of Chemistry

JF - Australian Journal of Chemistry

IS - 7

ER -

Preparation and chemistry of some 1-iodo-1-phenylpropenes

Abstract

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