Synthesis of 1,3-Divinylcyclopentane Derivatives from Platina(IV)cyclobutane Complexes

F. F. Stewart; W. D. Neilsen; R. E. Ekeland; R. D. Larsen; P. W. Jennings

doi:10.1021/om00035a050

Synthesis of 1,3-Divinylcyclopentane Derivatives from Platina(IV)cyclobutane Complexes

F. F. Stewart, W. D. Neilsen, R. E. Ekeland, R. D. Larsen, P. W. Jennings

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

13 Scopus citations

Abstract

A new transformation is reported in which a norbornyl-substituted platina(IV)cyclobutane complex is reacted with selected diazo derivatives to yield cis-1,3-divinylcyclopentane products in excellent yields. The distal substituent on one vinyl moiety is formed stereospecifically, while the substituent on the other vinyl moiety is not. Mechanistic details suggest a specific binding site for the diazo derivative leading to formation of a metallacyclopentane intermediate which spontaneously yields the divinyl product. The first crystal structure of a platina(IV)-cyclobutane bearing an electron-withdrawing aldehyde functionality is also included.

Original language	English
Pages (from-to)	4585-4591
Number of pages	7
Journal	Organometallics
Volume	12
Issue number	11
DOIs	https://doi.org/10.1021/om00035a050
State	Published - 1993
Externally published	Yes

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title = "Synthesis of 1,3-Divinylcyclopentane Derivatives from Platina(IV)cyclobutane Complexes",

abstract = "A new transformation is reported in which a norbornyl-substituted platina(IV)cyclobutane complex is reacted with selected diazo derivatives to yield cis-1,3-divinylcyclopentane products in excellent yields. The distal substituent on one vinyl moiety is formed stereospecifically, while the substituent on the other vinyl moiety is not. Mechanistic details suggest a specific binding site for the diazo derivative leading to formation of a metallacyclopentane intermediate which spontaneously yields the divinyl product. The first crystal structure of a platina(IV)-cyclobutane bearing an electron-withdrawing aldehyde functionality is also included.",

author = "Stewart, {F. F.} and Neilsen, {W. D.} and Ekeland, {R. E.} and Larsen, {R. D.} and Jennings, {P. W.}",

year = "1993",

doi = "10.1021/om00035a050",

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pages = "4585--4591",

journal = "Organometallics",

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T1 - Synthesis of 1,3-Divinylcyclopentane Derivatives from Platina(IV)cyclobutane Complexes

AU - Stewart, F. F.

AU - Neilsen, W. D.

AU - Ekeland, R. E.

AU - Larsen, R. D.

AU - Jennings, P. W.

PY - 1993

Y1 - 1993

N2 - A new transformation is reported in which a norbornyl-substituted platina(IV)cyclobutane complex is reacted with selected diazo derivatives to yield cis-1,3-divinylcyclopentane products in excellent yields. The distal substituent on one vinyl moiety is formed stereospecifically, while the substituent on the other vinyl moiety is not. Mechanistic details suggest a specific binding site for the diazo derivative leading to formation of a metallacyclopentane intermediate which spontaneously yields the divinyl product. The first crystal structure of a platina(IV)-cyclobutane bearing an electron-withdrawing aldehyde functionality is also included.

AB - A new transformation is reported in which a norbornyl-substituted platina(IV)cyclobutane complex is reacted with selected diazo derivatives to yield cis-1,3-divinylcyclopentane products in excellent yields. The distal substituent on one vinyl moiety is formed stereospecifically, while the substituent on the other vinyl moiety is not. Mechanistic details suggest a specific binding site for the diazo derivative leading to formation of a metallacyclopentane intermediate which spontaneously yields the divinyl product. The first crystal structure of a platina(IV)-cyclobutane bearing an electron-withdrawing aldehyde functionality is also included.

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U2 - 10.1021/om00035a050

DO - 10.1021/om00035a050

M3 - Article

AN - SCOPUS:0007978943

SN - 0276-7333

VL - 12

SP - 4585

EP - 4591

JO - Organometallics

JF - Organometallics

IS - 11

ER -

Synthesis of 1,3-Divinylcyclopentane Derivatives from Platina(IV)cyclobutane Complexes

Abstract

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