Preparation and X-ray crystal structures of two aliphatic selenenyl bromides stabilized by N-Se coordination

Thomas G. Back; Ziad Moussa; Masood Parvez

doi:10.1080/10426500490494543

Preparation and X-ray crystal structures of two aliphatic selenenyl bromides stabilized by N-Se coordination

Thomas G. Back, Ziad Moussa, Masood Parvez

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

9 Citations (Scopus)

Abstract

(1R)-2-endo-(Dimethylamino)methyl-2-exo-methoxy-3-endo-camphorylselenenyl bromide and its 2-endo-(pyrrolidenyl)methyl analogue were prepared from (1R)-2-endo-acetamidomethyl-2-exo-hydroxy-3-endo-camphoryl diselenide. Both compounds showed an unusual lack of reactivity in electrophilic oxyselenenylation and cyclization reactions that are typical of other selenenyl bromides. X-ray crystallography indicated that both compounds have strong N - Se interactions, with N - Se interatomic distances of ca. 2.1 Å, which diminish the electrophilic character of the selenium atom.

Original language	English
Pages (from-to)	2569-2579
Number of pages	11
Journal	Phosphorus, Sulfur and Silicon and the Related Elements
Volume	179
Issue number	12
DOIs	https://doi.org/10.1080/10426500490494543
Publication status	Published - Dec 2004
Externally published	Yes

Keywords

Electrophiles
N - Se coordination
Selenenyl bromides
X-ray structures

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Inorganic Chemistry

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10.1080/10426500490494543

Cite this

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title = "Preparation and X-ray crystal structures of two aliphatic selenenyl bromides stabilized by N-Se coordination",

abstract = "(1R)-2-endo-(Dimethylamino)methyl-2-exo-methoxy-3-endo-camphorylselenenyl bromide and its 2-endo-(pyrrolidenyl)methyl analogue were prepared from (1R)-2-endo-acetamidomethyl-2-exo-hydroxy-3-endo-camphoryl diselenide. Both compounds showed an unusual lack of reactivity in electrophilic oxyselenenylation and cyclization reactions that are typical of other selenenyl bromides. X-ray crystallography indicated that both compounds have strong N - Se interactions, with N - Se interatomic distances of ca. 2.1 {\AA}, which diminish the electrophilic character of the selenium atom.",

keywords = "Electrophiles, N - Se coordination, Selenenyl bromides, X-ray structures",

author = "Back, {Thomas G.} and Ziad Moussa and Masood Parvez",

note = "Funding Information: We thank the Natural Sciences and Engineering Research Council of Canada (NSERC) for financial support and Professor T. Chivers for some helpful comments.",

year = "2004",

month = dec,

doi = "10.1080/10426500490494543",

language = "English",

volume = "179",

pages = "2569--2579",

journal = "Phosphorus, Sulfur and Silicon and the Related Elements",

issn = "1042-6507",

publisher = "Taylor and Francis Ltd.",

number = "12",

}

TY - JOUR

T1 - Preparation and X-ray crystal structures of two aliphatic selenenyl bromides stabilized by N-Se coordination

AU - Back, Thomas G.

AU - Moussa, Ziad

AU - Parvez, Masood

N1 - Funding Information: We thank the Natural Sciences and Engineering Research Council of Canada (NSERC) for financial support and Professor T. Chivers for some helpful comments.

PY - 2004/12

Y1 - 2004/12

N2 - (1R)-2-endo-(Dimethylamino)methyl-2-exo-methoxy-3-endo-camphorylselenenyl bromide and its 2-endo-(pyrrolidenyl)methyl analogue were prepared from (1R)-2-endo-acetamidomethyl-2-exo-hydroxy-3-endo-camphoryl diselenide. Both compounds showed an unusual lack of reactivity in electrophilic oxyselenenylation and cyclization reactions that are typical of other selenenyl bromides. X-ray crystallography indicated that both compounds have strong N - Se interactions, with N - Se interatomic distances of ca. 2.1 Å, which diminish the electrophilic character of the selenium atom.

AB - (1R)-2-endo-(Dimethylamino)methyl-2-exo-methoxy-3-endo-camphorylselenenyl bromide and its 2-endo-(pyrrolidenyl)methyl analogue were prepared from (1R)-2-endo-acetamidomethyl-2-exo-hydroxy-3-endo-camphoryl diselenide. Both compounds showed an unusual lack of reactivity in electrophilic oxyselenenylation and cyclization reactions that are typical of other selenenyl bromides. X-ray crystallography indicated that both compounds have strong N - Se interactions, with N - Se interatomic distances of ca. 2.1 Å, which diminish the electrophilic character of the selenium atom.

KW - Electrophiles

KW - N - Se coordination

KW - Selenenyl bromides

KW - X-ray structures

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U2 - 10.1080/10426500490494543

DO - 10.1080/10426500490494543

M3 - Article

AN - SCOPUS:12444292078

SN - 1042-6507

VL - 179

SP - 2569

EP - 2579

JO - Phosphorus, Sulfur and Silicon and the Related Elements

JF - Phosphorus, Sulfur and Silicon and the Related Elements

IS - 12

ER -

Preparation and X-ray crystal structures of two aliphatic selenenyl bromides stabilized by N-Se coordination

Abstract

Keywords

ASJC Scopus subject areas

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