High Reactivity of Strained Seven-Membered-Ring trans-Alkenes

Jillian R. Sanzone, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

trans-Oxasilacycloheptenes are highly reactive strained alkenes. Competition reactions showed that these seven-membered ring trans-alkenes underwent [4+2] cycloaddition reactions faster than a trans-cyclooctene. They also reacted with quinones and dimethyl acetylenedicarboxylate to form adducts with high diastereoselectivity. Kinetic studies showed that ring strain increases nucleophilicity by approximately 109. trans-Oxasilacycloheptenes are strained seven-membered-ring trans-alkenes that underwent [4+2] cycloaddition reactions faster than a bicyclic trans-cyclooctene. They also reacted with quinones and dimethyl acetylenedicarboxylate to form adducts with high diastereoselectivity. Kinetic studies showed that ring strain increases nucleophilicity by approximately 109.

Original languageEnglish (US)
Pages (from-to)790-793
Number of pages4
JournalAngewandte Chemie - International Edition
Volume55
Issue number2
DOIs
StatePublished - Jan 11 2016

Fingerprint

Alkenes
Olefins
Quinones
Cycloaddition
Kinetics
acetylenedicarboxylic acid dimethyl ester

Keywords

  • alkenes
  • cycloaddition
  • cycloheptenes
  • silicon
  • strained molecules

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Cite this

High Reactivity of Strained Seven-Membered-Ring trans-Alkenes. / Sanzone, Jillian R.; Woerpel, Keith.

In: Angewandte Chemie - International Edition, Vol. 55, No. 2, 11.01.2016, p. 790-793.

Research output: Contribution to journalArticle

@article{01c3f5602a6d40ebb429d78ce13600a5,
title = "High Reactivity of Strained Seven-Membered-Ring trans-Alkenes",
abstract = "trans-Oxasilacycloheptenes are highly reactive strained alkenes. Competition reactions showed that these seven-membered ring trans-alkenes underwent [4+2] cycloaddition reactions faster than a trans-cyclooctene. They also reacted with quinones and dimethyl acetylenedicarboxylate to form adducts with high diastereoselectivity. Kinetic studies showed that ring strain increases nucleophilicity by approximately 109. trans-Oxasilacycloheptenes are strained seven-membered-ring trans-alkenes that underwent [4+2] cycloaddition reactions faster than a bicyclic trans-cyclooctene. They also reacted with quinones and dimethyl acetylenedicarboxylate to form adducts with high diastereoselectivity. Kinetic studies showed that ring strain increases nucleophilicity by approximately 109.",
keywords = "alkenes, cycloaddition, cycloheptenes, silicon, strained molecules",
author = "Sanzone, {Jillian R.} and Keith Woerpel",
year = "2016",
month = "1",
day = "11",
doi = "10.1002/anie.201510056",
language = "English (US)",
volume = "55",
pages = "790--793",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
number = "2",

}

TY - JOUR

T1 - High Reactivity of Strained Seven-Membered-Ring trans-Alkenes

AU - Sanzone, Jillian R.

AU - Woerpel, Keith

PY - 2016/1/11

Y1 - 2016/1/11

N2 - trans-Oxasilacycloheptenes are highly reactive strained alkenes. Competition reactions showed that these seven-membered ring trans-alkenes underwent [4+2] cycloaddition reactions faster than a trans-cyclooctene. They also reacted with quinones and dimethyl acetylenedicarboxylate to form adducts with high diastereoselectivity. Kinetic studies showed that ring strain increases nucleophilicity by approximately 109. trans-Oxasilacycloheptenes are strained seven-membered-ring trans-alkenes that underwent [4+2] cycloaddition reactions faster than a bicyclic trans-cyclooctene. They also reacted with quinones and dimethyl acetylenedicarboxylate to form adducts with high diastereoselectivity. Kinetic studies showed that ring strain increases nucleophilicity by approximately 109.

AB - trans-Oxasilacycloheptenes are highly reactive strained alkenes. Competition reactions showed that these seven-membered ring trans-alkenes underwent [4+2] cycloaddition reactions faster than a trans-cyclooctene. They also reacted with quinones and dimethyl acetylenedicarboxylate to form adducts with high diastereoselectivity. Kinetic studies showed that ring strain increases nucleophilicity by approximately 109. trans-Oxasilacycloheptenes are strained seven-membered-ring trans-alkenes that underwent [4+2] cycloaddition reactions faster than a bicyclic trans-cyclooctene. They also reacted with quinones and dimethyl acetylenedicarboxylate to form adducts with high diastereoselectivity. Kinetic studies showed that ring strain increases nucleophilicity by approximately 109.

KW - alkenes

KW - cycloaddition

KW - cycloheptenes

KW - silicon

KW - strained molecules

UR - http://www.scopus.com/inward/record.url?scp=84958114867&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84958114867&partnerID=8YFLogxK

U2 - 10.1002/anie.201510056

DO - 10.1002/anie.201510056

M3 - Article

VL - 55

SP - 790

EP - 793

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 2

ER -