Unexpected Rearrangement Leading to Formation of a 1,3-Bis(triphenylphosphonio)prop-1-en-3-idyl Carboxylate

R. Alan Aitken; Lee P. Cleghorn; Rebecca M. Leitch; Louis C. Morrill; Alexandra M. Z. Slawin

doi:10.1002/ejoc.201000143

Unexpected Rearrangement Leading to Formation of a 1,3-Bis(triphenylphosphonio)prop-1-en-3-idyl Carboxylate

R. Alan Aitken, Lee P. Cleghorn, Rebecca M. Leitch, Louis C. Morrill, Alexandra M. Z. Slawin

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

Abstract

Whereas bipheny1-4,4'-dicarbonyl dichloride reacts with methylenetriphenylphosphorane to give the expected bis-(acylylide) 1, the same reaction of biphenyl-2,2'-dicarbonyl dichloride results in a multistep rearrangement leading to the zwitterionic 2-[1,3-bis(triphenylphosphonio)prop-1-en-3-id-2-yl]bipheny1-2'-carboxylate 2. X-ray crystal structures of both 1 and 2 are reported.

Original language	English
Pages (from-to)	3211-3214
Number of pages	4
Journal	European Journal of Organic Chemistry
Volume	2010
Issue number	17
DOIs	https://doi.org/10.1002/ejoc.201000143
Publication status	Published - Jun 2010

Keywords

Rearrangement
Phosphorus
Ylides
PHOSPHORUS YLIDES
BU3P
DMAD

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10.1002/ejoc.201000143

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title = "Unexpected Rearrangement Leading to Formation of a 1,3-Bis(triphenylphosphonio)prop-1-en-3-idyl Carboxylate",

abstract = "Whereas bipheny1-4,4'-dicarbonyl dichloride reacts with methylenetriphenylphosphorane to give the expected bis-(acylylide) 1, the same reaction of biphenyl-2,2'-dicarbonyl dichloride results in a multistep rearrangement leading to the zwitterionic 2-[1,3-bis(triphenylphosphonio)prop-1-en-3-id-2-yl]bipheny1-2'-carboxylate 2. X-ray crystal structures of both 1 and 2 are reported.",

keywords = "Rearrangement, Phosphorus, Ylides, PHOSPHORUS YLIDES, BU3P, DMAD",

author = "Aitken, {R. Alan} and Cleghorn, {Lee P.} and Leitch, {Rebecca M.} and Morrill, {Louis C.} and Slawin, {Alexandra M. Z.}",

year = "2010",

month = jun,

doi = "10.1002/ejoc.201000143",

language = "English",

volume = "2010",

pages = "3211--3214",

journal = "European Journal of Organic Chemistry",

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publisher = "Wiley-VCH, Weinheim",

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T1 - Unexpected Rearrangement Leading to Formation of a 1,3-Bis(triphenylphosphonio)prop-1-en-3-idyl Carboxylate

AU - Aitken, R. Alan

AU - Cleghorn, Lee P.

AU - Leitch, Rebecca M.

AU - Morrill, Louis C.

AU - Slawin, Alexandra M. Z.

PY - 2010/6

Y1 - 2010/6

N2 - Whereas bipheny1-4,4'-dicarbonyl dichloride reacts with methylenetriphenylphosphorane to give the expected bis-(acylylide) 1, the same reaction of biphenyl-2,2'-dicarbonyl dichloride results in a multistep rearrangement leading to the zwitterionic 2-[1,3-bis(triphenylphosphonio)prop-1-en-3-id-2-yl]bipheny1-2'-carboxylate 2. X-ray crystal structures of both 1 and 2 are reported.

AB - Whereas bipheny1-4,4'-dicarbonyl dichloride reacts with methylenetriphenylphosphorane to give the expected bis-(acylylide) 1, the same reaction of biphenyl-2,2'-dicarbonyl dichloride results in a multistep rearrangement leading to the zwitterionic 2-[1,3-bis(triphenylphosphonio)prop-1-en-3-id-2-yl]bipheny1-2'-carboxylate 2. X-ray crystal structures of both 1 and 2 are reported.

KW - Rearrangement

KW - Phosphorus

KW - Ylides

KW - PHOSPHORUS YLIDES

KW - BU3P

KW - DMAD

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U2 - 10.1002/ejoc.201000143

DO - 10.1002/ejoc.201000143

M3 - Article

SN - 1434-193X

VL - 2010

SP - 3211

EP - 3214

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 17

ER -

Unexpected Rearrangement Leading to Formation of a 1,3-Bis(triphenylphosphonio)prop-1-en-3-idyl Carboxylate

Abstract

Keywords

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