Synthesis of cis,cis,cis,cis-[5.5.5.4]-1-azafenestrane with discovery of an unexpected dyotropic rearrangement

Scott E. Denmark; Justin I. Montgomery

doi:10.1002/anie.200500367

Synthesis of cis,cis,cis,cis-[5.5.5.4]-1-azafenestrane with discovery of an unexpected dyotropic rearrangement

Scott E. Denmark, Justin I. Montgomery

Chemistry

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

Abstract

(Figure Presented) An unprecedented skeletal reorganization initially hindered a concise route based on a tandem [4+2]/[3+2] nitroalkene cycloaddition for the synthesis of the strained title compound. Conditions to suppress the observed dyotropic rearrangement were developed, and X-ray crystallographic analysis of the BF₃ derivative (see picture) of the azafenestrane revealed significant planarization around the central carbon atom.

Original language	English (US)
Pages (from-to)	3732-3736
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	44
Issue number	24
DOIs	https://doi.org/10.1002/anie.200500367
State	Published - Jun 13 2005

Keywords

Cycloaddition
Dyotropic rearrangement
Fenestranes
Nitroalkenes
Strained molecules

ASJC Scopus subject areas

Catalysis
General Chemistry

Online availability

10.1002/anie.200500367

Library availability

Discover UIUC Full Text

Cite this

@article{0df707852de54dceb86c02f1e2c1c8b4,

title = "Synthesis of cis,cis,cis,cis-[5.5.5.4]-1-azafenestrane with discovery of an unexpected dyotropic rearrangement",

abstract = "(Figure Presented) An unprecedented skeletal reorganization initially hindered a concise route based on a tandem [4+2]/[3+2] nitroalkene cycloaddition for the synthesis of the strained title compound. Conditions to suppress the observed dyotropic rearrangement were developed, and X-ray crystallographic analysis of the BF3 derivative (see picture) of the azafenestrane revealed significant planarization around the central carbon atom.",

keywords = "Cycloaddition, Dyotropic rearrangement, Fenestranes, Nitroalkenes, Strained molecules",

author = "Denmark, {Scott E.} and Montgomery, {Justin I.}",

year = "2005",

month = jun,

day = "13",

doi = "10.1002/anie.200500367",

language = "English (US)",

volume = "44",

pages = "3732--3736",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley & Sons, Ltd.",

number = "24",

}

TY - JOUR

T1 - Synthesis of cis,cis,cis,cis-[5.5.5.4]-1-azafenestrane with discovery of an unexpected dyotropic rearrangement

AU - Denmark, Scott E.

AU - Montgomery, Justin I.

PY - 2005/6/13

Y1 - 2005/6/13

N2 - (Figure Presented) An unprecedented skeletal reorganization initially hindered a concise route based on a tandem [4+2]/[3+2] nitroalkene cycloaddition for the synthesis of the strained title compound. Conditions to suppress the observed dyotropic rearrangement were developed, and X-ray crystallographic analysis of the BF3 derivative (see picture) of the azafenestrane revealed significant planarization around the central carbon atom.

AB - (Figure Presented) An unprecedented skeletal reorganization initially hindered a concise route based on a tandem [4+2]/[3+2] nitroalkene cycloaddition for the synthesis of the strained title compound. Conditions to suppress the observed dyotropic rearrangement were developed, and X-ray crystallographic analysis of the BF3 derivative (see picture) of the azafenestrane revealed significant planarization around the central carbon atom.

KW - Cycloaddition

KW - Dyotropic rearrangement

KW - Fenestranes

KW - Nitroalkenes

KW - Strained molecules

UR - http://www.scopus.com/inward/record.url?scp=20444471621&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=20444471621&partnerID=8YFLogxK

U2 - 10.1002/anie.200500367

DO - 10.1002/anie.200500367

M3 - Article

C2 - 15887203

AN - SCOPUS:20444471621

SN - 1433-7851

VL - 44

SP - 3732

EP - 3736

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 24

ER -

Synthesis of cis,cis,cis,cis-[5.5.5.4]-1-azafenestrane with discovery of an unexpected dyotropic rearrangement

Abstract

Keywords

ASJC Scopus subject areas

Online availability

Library availability

Related links

Fingerprint

Cite this