A planar silacyclobutane, 1,1-(rac-1,1′-bi-2-naphthoxy)-1- silacyclobutane and its unusual reaction with bis(1,5-cyclooctadiene)platinum(0)

Rajsapan Jain; Andrew P.J. Brunskill; John B. Sheridan; Roger A. Lalancette

doi:10.1016/j.jorganchem.2005.02.032

A planar silacyclobutane, 1,1-(rac-1,1′-bi-2-naphthoxy)-1- silacyclobutane and its unusual reaction with bis(1,5-cyclooctadiene)platinum(0)

Rajsapan Jain, Andrew P.J. Brunskill, John B. Sheridan, Roger A. Lalancette

SASN Chemistry

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

8 Scopus citations

Abstract

The synthesis, characterization and X-ray crystal structure of 1,1-(rac-1,1′-bi-2-naphthoxy)-1-silacyclobutane (1) are reported and reveal an unusual planar conformation with a Si-βC distance of 2.302 (5) Å. Reaction of 1 with either stoichiometric or catalytic amounts of bis(1,5-cyclooctadiene)platinum(0) {Pt(cod)₂} gave 1,1′-bi-2-naphthol (BINOL), rather than the expected insertion products or polymer. A mechanism is proposed based on insertion of the Pt(cod) into 1 followed by hydride transfers via the Pt center to the 1,1′-bi-2-naphthoxy group. Anionic ring-opening polymerization of 1 is also reported and gave the poly(carbosilane) (4).

Original language	English (US)
Pages (from-to)	2272-2277
Number of pages	6
Journal	Journal of Organometallic Chemistry
Volume	690
Issue number	9
DOIs	https://doi.org/10.1016/j.jorganchem.2005.02.032
State	Published - Apr 29 2005

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

Keywords

Platinum-catalyzed
Silacyclobutane

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title = "A planar silacyclobutane, 1,1-(rac-1,1′-bi-2-naphthoxy)-1- silacyclobutane and its unusual reaction with bis(1,5-cyclooctadiene)platinum(0)",

abstract = "The synthesis, characterization and X-ray crystal structure of 1,1-(rac-1,1′-bi-2-naphthoxy)-1-silacyclobutane (1) are reported and reveal an unusual planar conformation with a Si-βC distance of 2.302 (5) {\AA}. Reaction of 1 with either stoichiometric or catalytic amounts of bis(1,5-cyclooctadiene)platinum(0) {Pt(cod)2} gave 1,1′-bi-2-naphthol (BINOL), rather than the expected insertion products or polymer. A mechanism is proposed based on insertion of the Pt(cod) into 1 followed by hydride transfers via the Pt center to the 1,1′-bi-2-naphthoxy group. Anionic ring-opening polymerization of 1 is also reported and gave the poly(carbosilane) (4).",

keywords = "Platinum-catalyzed, Silacyclobutane",

author = "Rajsapan Jain and Brunskill, {Andrew P.J.} and Sheridan, {John B.} and Lalancette, {Roger A.}",

year = "2005",

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doi = "10.1016/j.jorganchem.2005.02.032",

language = "English (US)",

volume = "690",

pages = "2272--2277",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier",

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A planar silacyclobutane, 1,1-(rac-1,1′-bi-2-naphthoxy)-1- silacyclobutane and its unusual reaction with bis(1,5-cyclooctadiene)platinum(0). / Jain, Rajsapan; Brunskill, Andrew P.J.; Sheridan, John B.; Lalancette, Roger A.

In: Journal of Organometallic Chemistry, Vol. 690, No. 9, 29.04.2005, p. 2272-2277.

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

TY - JOUR

T1 - A planar silacyclobutane, 1,1-(rac-1,1′-bi-2-naphthoxy)-1- silacyclobutane and its unusual reaction with bis(1,5-cyclooctadiene)platinum(0)

AU - Jain, Rajsapan

AU - Brunskill, Andrew P.J.

AU - Sheridan, John B.

AU - Lalancette, Roger A.

PY - 2005/4/29

Y1 - 2005/4/29

N2 - The synthesis, characterization and X-ray crystal structure of 1,1-(rac-1,1′-bi-2-naphthoxy)-1-silacyclobutane (1) are reported and reveal an unusual planar conformation with a Si-βC distance of 2.302 (5) Å. Reaction of 1 with either stoichiometric or catalytic amounts of bis(1,5-cyclooctadiene)platinum(0) {Pt(cod)2} gave 1,1′-bi-2-naphthol (BINOL), rather than the expected insertion products or polymer. A mechanism is proposed based on insertion of the Pt(cod) into 1 followed by hydride transfers via the Pt center to the 1,1′-bi-2-naphthoxy group. Anionic ring-opening polymerization of 1 is also reported and gave the poly(carbosilane) (4).

AB - The synthesis, characterization and X-ray crystal structure of 1,1-(rac-1,1′-bi-2-naphthoxy)-1-silacyclobutane (1) are reported and reveal an unusual planar conformation with a Si-βC distance of 2.302 (5) Å. Reaction of 1 with either stoichiometric or catalytic amounts of bis(1,5-cyclooctadiene)platinum(0) {Pt(cod)2} gave 1,1′-bi-2-naphthol (BINOL), rather than the expected insertion products or polymer. A mechanism is proposed based on insertion of the Pt(cod) into 1 followed by hydride transfers via the Pt center to the 1,1′-bi-2-naphthoxy group. Anionic ring-opening polymerization of 1 is also reported and gave the poly(carbosilane) (4).

KW - Platinum-catalyzed

KW - Silacyclobutane

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DO - 10.1016/j.jorganchem.2005.02.032

M3 - Article

AN - SCOPUS:17444392089

VL - 690

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JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

IS - 9

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A planar silacyclobutane, 1,1-(rac-1,1′-bi-2-naphthoxy)-1- silacyclobutane and its unusual reaction with bis(1,5-cyclooctadiene)platinum(0)

Abstract

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