Carbenes from cyclopropanated aromatics

AD Roth, DM Thamattoor - Organic & Biomolecular Chemistry, 2023 - pubs.rsc.org
Although a ripe old discipline by now, carbene chemistry continues to flourish as both
theorists and experimentalists have shown sustained interest in this area of research. While …

Adamantylidenecarbene: photochemical generation, trapping, and theoretical studies

AD Roth, CE Wamsley, SM Haynes… - The Journal of Organic …, 2023 - ACS Publications
Photolysis of 1-(2-adamantylidene)-1a, 9b-dihydro-1 H-cyclopropa [l] phenanthrene in
benzene (or benzene-d 6) at ambient temperature produces adamantylidenecarbene. The …

Systematic evaluation of 1, 2-migratory aptitude in alkylidene carbenes

HJA Dale, C Nottingham, C Poree… - Journal of the …, 2021 - ACS Publications
Alkylidene carbenes undergo rapid inter-and intramolecular reactions and rearrangements,
including 1, 2-migrations of β-substituents to generate alkynes. Their propensity for …

Detection of Ylide Formation between an Alkylidenecarbene and Acetonitrile by Femtosecond Transient Absorption Spectroscopy

SK Sarkar, M Ko, X Bai, L Du… - Journal of the …, 2021 - ACS Publications
Femtosecond laser flash photolysis of 3-(1 a, 9 b-dihydro-1 H-cyclopropa [l] phenanthren-1-
ylidene) tetrahydrofuran produces singlet 3-oxacyclopentylidenecarbene which reacts with …

Direct observation of the dynamics of ylide solvation by hydrogen-bond donors using time-resolved infrared spectroscopy

R Phelps, AJ Orr-Ewing - Journal of the American Chemical …, 2022 - ACS Publications
The photoexcitation of α-diazocarbonyl compounds produces singlet carbene intermediates
that react with nucleophilic solvent molecules to form ylides. The zwitterionic nature of these …

Polymorphism in 9-[(9H-Fluoren-9-ylidene)methyl]phenanthrene

AD Roth, DM Thamattoor - Crystal Growth & Design, 2022 - ACS Publications
Three polymorphs of the hydrocarbon 9-[(9 H-fluoren-9-ylidene) methyl] phenanthrene have
been isolated and characterized by single-crystal X-ray crystallography. Of these, one form …

Bent Singlet Cyclobutylcarbene: Computed Geometry, Properties, and Product Selectivity of a Nonclassical Carbene

MG Rosenberg, UH Brinker - The Journal of Organic Chemistry, 2019 - ACS Publications
Ab initio computations of cyclobutylcarbene (c-C4H7CH) were performed using the UMP4
(fc)/6-311++ G (2df, 2p)//UMP2 (full)/6-311++ G (d, p) theoretical model. The carbene's most …

Characterization of a triplet vinylidene

Y Kutin, J Reitz, PW Antoni, A Savitsky… - Journal of the …, 2021 - ACS Publications
Singlet vinylidenes (R2C═ C:) are proposed as intermediates in a series of organic
reactions, and very few have been studied by matrix isolation or gas-phase spectroscopy …

Generation and Capture of Both Sides of the 7-Norbornylidene—Bicyclo [2.2. 2] oct-2-yne Fritsch–Buttenberg–Wiechell Rearrangement

D Thamattoor - 2023 - researchsquare.com
The strained caged alkyne bicyclo [2.2. 2] oct-2-yne, previously reported to be inaccessible,
was generated via the Fritsch–Buttenberg–Wiechell rearrangement of 7-norbornylidene …

Ring Expansion of Alkylidenecarbenes Derived from Lactams, Lactones, and Thiolactones into Strained Heterocyclic Alkynes: A Theoretical Study

NNT Le, J Just, JM Pankauski, PR Rablen… - Molecules, 2019 - mdpi.com
Strained cycloalkynes are of considerable interest to theoreticians and experimentalists, and
possess much synthetic value as well. Herein, a series of cyclic alkylidenecarbenes …