A Facile Preparation of N-Heterocyclic Olefins: Ring-Opening Polymerization of β-Butyrolactone and Frustrated Lewis Pair Reactivity**

Natesan Mannangatti Rajendran; Qi Lu; Jean Bouffard

doi:10.1002/chem.202303358

A Facile Preparation of N-Heterocyclic Olefins: Ring-Opening Polymerization of β-Butyrolactone and Frustrated Lewis Pair Reactivity**

Natesan Mannangatti Rajendran
, Qi Lu
, Jean Bouffard

Department of Chemistry & Nanoscience

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

4 Scopus citations

Abstract

A direct synthesis of N-heterocyclic olefins (NHOs) and their mesoionic congeners (mNHOs) from N-heterocyclic carbenes and N-aziridinylimines is reported. The reaction provided diverse functionalized (m)NHOs and π-extended analogues. The prepared NHOs initiated the ring-opening polymerization of β-butyrolactone, and insertion of aldehyde and nitrile into an NHO-B(C₆F₅)₃ adduct was demonstrated.

Original language	English
Article number	e202303358
Journal	Chemistry - A European Journal
Volume	30
Issue number	8
DOIs	https://doi.org/10.1002/chem.202303358
State	Published - 7 Feb 2024

Bibliographical note

Publisher Copyright:
© 2023 Wiley-VCH GmbH.

Keywords

N-Heterocyclic olefins
N-aziridinylimine
N-heterocyclic carbenes
frustrated Lewis pairs
polymerization

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10.1002/chem.202303358

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title = "A Facile Preparation of N-Heterocyclic Olefins: Ring-Opening Polymerization of β-Butyrolactone and Frustrated Lewis Pair Reactivity**",

abstract = "A direct synthesis of N-heterocyclic olefins (NHOs) and their mesoionic congeners (mNHOs) from N-heterocyclic carbenes and N-aziridinylimines is reported. The reaction provided diverse functionalized (m)NHOs and π-extended analogues. The prepared NHOs initiated the ring-opening polymerization of β-butyrolactone, and insertion of aldehyde and nitrile into an NHO-B(C6F5)3 adduct was demonstrated.",

keywords = "N-Heterocyclic olefins, N-aziridinylimine, N-heterocyclic carbenes, frustrated Lewis pairs, polymerization",

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T2 - Ring-Opening Polymerization of β-Butyrolactone and Frustrated Lewis Pair Reactivity**

AU - Rajendran, Natesan Mannangatti

AU - Lu, Qi

AU - Bouffard, Jean

PY - 2024/2/7

Y1 - 2024/2/7

N2 - A direct synthesis of N-heterocyclic olefins (NHOs) and their mesoionic congeners (mNHOs) from N-heterocyclic carbenes and N-aziridinylimines is reported. The reaction provided diverse functionalized (m)NHOs and π-extended analogues. The prepared NHOs initiated the ring-opening polymerization of β-butyrolactone, and insertion of aldehyde and nitrile into an NHO-B(C6F5)3 adduct was demonstrated.

AB - A direct synthesis of N-heterocyclic olefins (NHOs) and their mesoionic congeners (mNHOs) from N-heterocyclic carbenes and N-aziridinylimines is reported. The reaction provided diverse functionalized (m)NHOs and π-extended analogues. The prepared NHOs initiated the ring-opening polymerization of β-butyrolactone, and insertion of aldehyde and nitrile into an NHO-B(C6F5)3 adduct was demonstrated.

KW - N-Heterocyclic olefins

KW - N-aziridinylimine

KW - N-heterocyclic carbenes

KW - frustrated Lewis pairs

KW - polymerization

UR - https://www.scopus.com/pages/publications/85179950287

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DO - 10.1002/chem.202303358

M3 - Article

C2 - 38109087

AN - SCOPUS:85179950287

SN - 0947-6539

VL - 30

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 8

M1 - e202303358

ER -

A Facile Preparation of N-Heterocyclic Olefins: Ring-Opening Polymerization of β-Butyrolactone and Frustrated Lewis Pair Reactivity**

Abstract

Bibliographical note

Keywords

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