Changing the path of least resistance, or access to endo-dig products via a sequence of three exo-trig transition states: electronic effects in homoallyic ring expansion cascades of alkenyl isonitriles-Reference-Cited by-同舟云学术

Changing the path of least resistance, or access to endo-dig products via a sequence of three exo-trig transition states: electronic effects in homoallyic ring expansion cascades of alkenyl isonitriles

Published:2017 Issue:19 Volume:15 Page:4135-4143
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Gomes Gabriel dos Passos¹²³⁴^ORCID,Evoniuk Christopher J.¹²³⁴,Ly Michelle¹²³⁴,Alabugin Igor V.¹²³⁴

Affiliation:

1. Department of Chemistry and Biochemistry

2. Florida State University

3. Tallahassee

4. USA

Abstract

Substituent effects reshape the potential energy surfaces for radical homoallylic expansion/fragmentation cascades that transform alkenyl isonitriles into N-heteroaromatics

Funder

Division of Chemistry

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2017/OB/C7OB00527J

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1. Rate constants and Arrhenius functions for rearrangements of the 2,2-dimethyl-3-butenyl and (2,2-dimethylcyclopropyl)methyl radicals

2. Kinetics and regioselectivity of ring opening of substituted cyclopropylmethyl radicals

3. Cascading Radical Cyclization of Bis-Vinyl Ethers: Mechanistic Investigation Reveals a 5-exo/3-exo/retro-3-exo/5-exo Pathway