Novel synthesis of alkenes via triethylaluminum-induced free radical reactions of alkyl iodides and β-nitrostyrenes

Jing Yuan Liu; Ju Tsung Liu; Ching Fa Yao

doi:10.1016/S0040-4039(01)00519-6

Novel synthesis of alkenes via triethylaluminum-induced free radical reactions of alkyl iodides and β-nitrostyrenes

Jing Yuan Liu
, Ju Tsung Liu
, Ching Fa Yao^*

^*Corresponding author for this work

Department of Chemistry

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

26 Citations (Scopus)

Abstract

Reactions of (E)-β-nitrostyrenes 1 with triethylaluminum (Et₃Al) 2 and alkyl iodide (RI) 3, 4, or 5 in the presence of benzoyl peroxide in diethyl ether solution at room temperature to give 60-100% of the different (E)-alkenes 6, 7, or 8. Under similar conditions, 95% of 1-adamantyl-2-(4-methoxyphenyl)ethene 10 or 80% of 1-(4-oxoadamantyl)-2-(4-methoxyphenyl)ethene 12 also can be easily prepared by using 1-iodoadamantane 9 or 5-iodo-2-adamantanone 11 and 2.

Original language	English
Pages (from-to)	3613-3615
Number of pages	3
Journal	Tetrahedron Letters
Volume	42
Issue number	21
DOIs	https://doi.org/10.1016/S0040-4039(01)00519-6
Publication status	Published - 2001 May 21

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(01)00519-6

Cite this

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title = "Novel synthesis of alkenes via triethylaluminum-induced free radical reactions of alkyl iodides and β-nitrostyrenes",

abstract = "Reactions of (E)-β-nitrostyrenes 1 with triethylaluminum (Et3Al) 2 and alkyl iodide (RI) 3, 4, or 5 in the presence of benzoyl peroxide in diethyl ether solution at room temperature to give 60-100\% of the different (E)-alkenes 6, 7, or 8. Under similar conditions, 95\% of 1-adamantyl-2-(4-methoxyphenyl)ethene 10 or 80\% of 1-(4-oxoadamantyl)-2-(4-methoxyphenyl)ethene 12 also can be easily prepared by using 1-iodoadamantane 9 or 5-iodo-2-adamantanone 11 and 2.",

author = "Liu, \{Jing Yuan\} and Liu, \{Ju Tsung\} and Yao, \{Ching Fa\}",

note = "Funding Information: Financial support of this work by the National Science Council of the Republic of China is gratefully acknowledged. ",

year = "2001",

month = may,

day = "21",

doi = "10.1016/S0040-4039(01)00519-6",

language = "English",

volume = "42",

pages = "3613--3615",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "21",

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TY - JOUR

T1 - Novel synthesis of alkenes via triethylaluminum-induced free radical reactions of alkyl iodides and β-nitrostyrenes

AU - Liu, Jing Yuan

AU - Liu, Ju Tsung

AU - Yao, Ching Fa

N1 - Funding Information: Financial support of this work by the National Science Council of the Republic of China is gratefully acknowledged.

PY - 2001/5/21

Y1 - 2001/5/21

N2 - Reactions of (E)-β-nitrostyrenes 1 with triethylaluminum (Et3Al) 2 and alkyl iodide (RI) 3, 4, or 5 in the presence of benzoyl peroxide in diethyl ether solution at room temperature to give 60-100% of the different (E)-alkenes 6, 7, or 8. Under similar conditions, 95% of 1-adamantyl-2-(4-methoxyphenyl)ethene 10 or 80% of 1-(4-oxoadamantyl)-2-(4-methoxyphenyl)ethene 12 also can be easily prepared by using 1-iodoadamantane 9 or 5-iodo-2-adamantanone 11 and 2.

AB - Reactions of (E)-β-nitrostyrenes 1 with triethylaluminum (Et3Al) 2 and alkyl iodide (RI) 3, 4, or 5 in the presence of benzoyl peroxide in diethyl ether solution at room temperature to give 60-100% of the different (E)-alkenes 6, 7, or 8. Under similar conditions, 95% of 1-adamantyl-2-(4-methoxyphenyl)ethene 10 or 80% of 1-(4-oxoadamantyl)-2-(4-methoxyphenyl)ethene 12 also can be easily prepared by using 1-iodoadamantane 9 or 5-iodo-2-adamantanone 11 and 2.

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UR - https://www.scopus.com/pages/publications/0035926282#tab=citedBy

U2 - 10.1016/S0040-4039(01)00519-6

DO - 10.1016/S0040-4039(01)00519-6

M3 - Article

AN - SCOPUS:0035926282

SN - 0040-4039

VL - 42

SP - 3613

EP - 3615

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 21

ER -

Novel synthesis of alkenes via triethylaluminum-induced free radical reactions of alkyl iodides and β-nitrostyrenes

Abstract

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