Diastereoselective formation of complexed methylenediphosphiranes

Helen Jansen; Amos J. Rosenthal; J. Chris Slootweg; Andreas W. Ehlers; Martin Lutz; Anthony L. Spek; Koop Lammertsma

doi:10.1021/om800188h

Diastereoselective formation of complexed methylenediphosphiranes

Helen Jansen, Amos J. Rosenthal, J. Chris Slootweg, Andreas W. Ehlers, Martin Lutz, Anthony L. Spek, Koop Lammertsma

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

6 Citations (Scopus)

Abstract

Stable syn-substituted methylenediphosphirane complexes are obtained from the reaction of transient, electrophilic phosphinidenes [R-P=W(CO)₅] (R = Me, Ph), thermally generated from the corresponding benzophosphepines, with 1-phosphaallene. A DFT analysis at the B3PW91/6-31G(d) level of theory reveals that the high diastereoselectivity of this reaction results from the preferred negative activation energy for syn cyclization of the P,P-ylide intermediates.

Original language	English
Pages (from-to)	2868-2872
Number of pages	5
Journal	Organometallics
Volume	27
Issue number	12
DOIs	https://doi.org/10.1021/om800188h
Publication status	Published - 23 Jun 2008
Externally published	Yes

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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title = "Diastereoselective formation of complexed methylenediphosphiranes",

abstract = "Stable syn-substituted methylenediphosphirane complexes are obtained from the reaction of transient, electrophilic phosphinidenes [R-P=W(CO)5] (R = Me, Ph), thermally generated from the corresponding benzophosphepines, with 1-phosphaallene. A DFT analysis at the B3PW91/6-31G(d) level of theory reveals that the high diastereoselectivity of this reaction results from the preferred negative activation energy for syn cyclization of the P,P-ylide intermediates.",

author = "Helen Jansen and Rosenthal, {Amos J.} and {Chris Slootweg}, J. and Ehlers, {Andreas W.} and Martin Lutz and Spek, {Anthony L.} and Koop Lammertsma",

year = "2008",

month = jun,

day = "23",

doi = "10.1021/om800188h",

language = "English",

volume = "27",

pages = "2868--2872",

journal = "Organometallics",

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publisher = "American Chemical Society",

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TY - JOUR

T1 - Diastereoselective formation of complexed methylenediphosphiranes

AU - Jansen, Helen

AU - Rosenthal, Amos J.

AU - Chris Slootweg, J.

AU - Ehlers, Andreas W.

AU - Lutz, Martin

AU - Spek, Anthony L.

AU - Lammertsma, Koop

PY - 2008/6/23

Y1 - 2008/6/23

N2 - Stable syn-substituted methylenediphosphirane complexes are obtained from the reaction of transient, electrophilic phosphinidenes [R-P=W(CO)5] (R = Me, Ph), thermally generated from the corresponding benzophosphepines, with 1-phosphaallene. A DFT analysis at the B3PW91/6-31G(d) level of theory reveals that the high diastereoselectivity of this reaction results from the preferred negative activation energy for syn cyclization of the P,P-ylide intermediates.

AB - Stable syn-substituted methylenediphosphirane complexes are obtained from the reaction of transient, electrophilic phosphinidenes [R-P=W(CO)5] (R = Me, Ph), thermally generated from the corresponding benzophosphepines, with 1-phosphaallene. A DFT analysis at the B3PW91/6-31G(d) level of theory reveals that the high diastereoselectivity of this reaction results from the preferred negative activation energy for syn cyclization of the P,P-ylide intermediates.

UR - http://www.scopus.com/inward/record.url?scp=47249091896&partnerID=8YFLogxK

U2 - 10.1021/om800188h

DO - 10.1021/om800188h

M3 - Article

AN - SCOPUS:47249091896

SN - 0276-7333

VL - 27

SP - 2868

EP - 2872

JO - Organometallics

JF - Organometallics

IS - 12

ER -

Diastereoselective formation of complexed methylenediphosphiranes

Abstract

ASJC Scopus subject areas

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