Trienediynes on a 1,3,5-trisubstituted benzene template: a new approach for enhancement of reactivity

Ishita Hatial, Saibal Jana, Shrabani Bisai, Manasmita Das, Ananta Kumar Ghosh, Anakuthil Anoop and Amit Basak

RSC Adv., 2014, 4, 28041
DOI: 10.1039/c4ra04794j

Nucleus-Independent Chemical Shifts (NICS) as an Aromaticity Criterion

Zhongfang Chen, Chaitanya S. Wannere, Clémence Corminboeuf, Ralph Puchta and Paul von Ragué Schleyer

Chem. Rev., 2005, 105, 3842
DOI: 10.1021/cr030088+

Systematic comparison of the benzynes, pyridynes, and pyridynium cations and characterization of the Bergman cyclization of Z-but-1-en-3-yn-1-yl isonitrile to the meta diradical 2,4-pyridyne

Stefan L Debbert and Christopher J Cramer

International Journal of Mass Spectrometry, 2000, 201, 1
DOI: 10.1016/S1387-3806(00)00160-3

Cyclohexeno[3,4]cyclodec-1,5-diyne-3-ene: A Convenient Enediyne

Annadka Shrinidhi and Charles L. Perrin

Org. Lett., 2021, 23, 6911
DOI: 10.1021/acs.orglett.1c02459

Substituent effects on the Bergman cyclization of (Z)‐1,5‐hexadiyne‐3‐enes: a systematic computational study

Matthias Prall, Alexander Wittkopp, Andrey A. Fokin and Peter R. Schreiner

J Comput Chem, 2001, 22, 1605
DOI: 10.1002/jcc.1114

Mechanical Manipulation of Chemical Reactions: Reactivity Switching of Bergman Cyclizations

Martin Krupička, Wolfram Sander and Dominik Marx

J. Phys. Chem. Lett., 2014, 5, 905
DOI: 10.1021/jz402644e

Theoretical Study of the Reaction Mechanisms Involved in the Thermal Intramolecular Reactions of 1,6-Fullerenynes

Mireia Güell, Nazario Martín, Margarita Altable, Salvatore Filippone, Ángel Martín-Domenech and Miquel Solà

J. Phys. Chem. A, 2007, 111, 5253
DOI: 10.1021/jp0705368

High carbon yielding and melt processable bis-ortho-diynylarene (BODA)-derived resins for rapid processing of dense carbon/carbon composites

Ernesto I. Borrego, Sumudu Athukorale, Saidulu Gorla, Alison K. Duckworth, Myles Baker, Jonathan Rosales, William W. Johnson, Santanu Kundu, Hossein Toghiani, Behzad Farajidizaji, Charles U. Pittman and Dennis W. Smith

Composites Part B: Engineering, 2022, 242, 110080
DOI: 10.1016/j.compositesb.2022.110080

Electronic Effects on the Bergman Cyclisation of Enediynes. A Review

Michael Klein, Thomas Walenzyk and Burkhard König

Collect. Czech. Chem. Commun., 2004, 69, 945
DOI: 10.1135/cccc20040945

Thepara-didehydropyridine,para-didehydropyridinium, and related biradicals?a contribution to the chemistry of enediyne antitumor drugs

Elfi Kraka and Dieter Cremer

J. Comput. Chem., 2001, 22, 216
DOI: 10.1002/1096-987X(20010130)22:2<216::AID-JCC9>3.0.CO;2-X

Influence of Hydroxyl Substitution on Benzyne Properties. Quantum Chemical Characterization of the Didehydrophenols

William T. G. Johnson and Christopher J. Cramer

J. Am. Chem. Soc., 2001, 123, 923
DOI: 10.1021/ja002250l

Quantum Chemical Characterization of Singlet and Triplet Didehydroindenes

Christopher J. Cramer and Jason Thompson

J. Phys. Chem. A, 2001, 105, 2091
DOI: 10.1021/jp004379n

Mechanism of the Intramolecular Hexadehydro-Diels–Alder Reaction

Daniel J. Marell, Lawrence R. Furan, Brian P. Woods, Xiangyun Lei, Andrew J. Bendelsmith, Christopher J. Cramer, Thomas R. Hoye and Keith T. Kuwata

J. Org. Chem., 2015, 80, 11744
DOI: 10.1021/acs.joc.5b01356

Towards Isocoumarin‐Fused Enediyne Systems through the Electrophilic Cyclization of Methyl o‐(Buta‐1,3‐diynyl)benzoates

Natalia A. Danilkina, Larisa Y. Gurskaya, Aleksander V. Vasilyev and Irina A. Balova

Eur J Org Chem, 2016, 2016, 739
DOI: 10.1002/ejoc.201501262

Moderating Strain without Sacrificing Reactivity: Design of Fast and Tunable Noncatalyzed Alkyne–Azide Cycloadditions via Stereoelectronically Controlled Transition State Stabilization

Brian Gold, Gregory B. Dudley and Igor V. Alabugin

J. Am. Chem. Soc., 2013, 135, 1558
DOI: 10.1021/ja3114196

Analytic gradients for the state-specific multireference coupled cluster singles and doubles model

Eric Prochnow, Francesco A. Evangelista, Henry F. Schaefer, Wesley D. Allen and Jürgen Gauss

The Journal of Chemical Physics, 2009, 131
DOI: 10.1063/1.3204017

Relative Reactivity of Benzothiophene-Fused Enediynes in the Bergman Cyclization

Anna G. Lyapunova, Natalia A. Danilkina, Andrey M. Rumyantsev, A. F. Khlebnikov, Mikhail V. Chislov, Galina L. Starova, Elena V. Sambuk, Anastasia I. Govdi, Stefan Bräse and Irina A. Balova

J. Org. Chem., 2018, 83, 2788
DOI: 10.1021/acs.joc.7b03258

The Cyclization of Parent and Cyclic Hexa-1,3-dien-5-ynes—A Combined Theoretical and Experimental Study

Matthias Prall, Anke Krüger, Peter R. Schreiner and Henning Hopf

Chem. Eur. J., 2001, 7, 4386
DOI: 10.1002/1521-3765(20011015)7:20<4386::AID-CHEM4386>3.0.CO;2-S

A Jahn−Teller Geometric Distortion Effect on the Woodward−Hoffmann Rule in Thermal Decompositions of Diazetines

Shinichi Yamabe and Tsutomu Minato

J. Phys. Chem. A, 2001, 105, 7281
DOI: 10.1021/jp0106808

Density Functional Study of the Ring Effect on the Myers−Saito Cyclization and a Comparison with the Bergman Cyclization

Chen, Jian-Wei Zou and Chin-Hui Yu

J. Org. Chem., 2003, 68, 3663
DOI: 10.1021/jo0267246

IR study of temperature induced rearrangements of dehydrobenzoannulenes

Boris Zimmermann, Goran Baranović and Jelena Macan

Vibrational Spectroscopy, 2007, 43, 38
DOI: 10.1016/j.vibspec.2006.06.007

Theoretische Chemie 1998

Dominik Marx, Bernd Engels, Michael Bühl and Peter Saalfrunk

Nachr. Chem. Tech. Lab., 1999, 47, 186
DOI: 10.1002/nadc.19990470212

Tetraborylation of p-Benzynes Generated by the Masamune–Bergman Cyclization through Reaction Design Based on the Reaction Path Network

Soichiro Nakatsuka, Seiji Akiyama, Yu Harabuchi, Satoshi Maeda and Yuuya Nagata

JACS Au, 2024, 4, 2578
DOI: 10.1021/jacsau.4c00302

Tetradehydrobenzenes: Singlet−Triplet Energy Separations and Vibrational Frequencies

Holger F. Bettinger, Paul v. R. Schleyer and Henry F. Schaefer

J. Am. Chem. Soc., 1999, 121, 2829
DOI: 10.1021/ja981681p

Electrophilic Cyclization and Ring‐Closing Metathesis as Key Steps in the Synthesis of a 12‐Membered Cyclic Enediyne

Natalia Danilkina, Martin Nieger, Stanislav Selivanov, Stefan Bräse and Irina Balova

Eur J Org Chem, 2012, 2012, 5660
DOI: 10.1002/ejoc.201200881

Multireference Averaged Quadratic Coupled Cluster (MR-AQCC) Study of the Geometries and Energies for ortho-, meta- and para-Benzyne

Khanh Vu, Joshua Pandian, Boyi Zhang, Christina Annas, Anna J. Parker, John S. Mancini, Evan B. Wang, Diomedes Saldana-Greco, Emily S. Nelson, Greg Springsted, Hans Lischka, Felix Plasser and Carol A. Parish

J. Phys. Chem. A, 2024, 128, 7816
DOI: 10.1021/acs.jpca.4c04099

The bergman cyclizations of the enediyne and its N‐substituted analogs using multiconfigurational second‐order perturbation theory

Hua Dong, Bo‐Zhen Chen, Ming‐Bao Huang and Roland Lindh

J Comput Chem, 2012, 33, 537
DOI: 10.1002/jcc.22889

Concerted Reactions That Produce Diradicals and Zwitterions: Electronic, Steric, Conformational, and Kinetic Control of Cycloaromatization Processes

Rana K. Mohamed, Paul W. Peterson and Igor V. Alabugin

Chem. Rev., 2013, 113, 7089
DOI: 10.1021/cr4000682

Can Unrestricted Density-Functional Theory Describe Open Shell Singlet Biradicals?

Jürgen Gräfenstein, Elfi Kraka, Michael Filatov and Dieter Cremer

IJMS, 2002, 3, 360
DOI: 10.3390/i3040360

Design, synthesis and inhibition activity of a novel cyclic enediyne amino acid conjugates against MPtpA

Koushik Chandra, Debajyoti Dutta, Analava Mitra, Amit K. Das and Amit Basak

Bioorganic & Medicinal Chemistry, 2011, 19, 3274
DOI: 10.1016/j.bmc.2011.03.024

Matrix Isolation and Spectroscopic Characterization of Perfluorinatedortho- andmeta-Benzyne

Hans Henning Wenk and Wolfram Sander

Chem. Eur. J., 2001, 7, 1837
DOI: 10.1002/1521-3765(20010504)7:9<1837::AID-CHEM1837>3.0.CO;2-T

Electronic Interactions in Aryne Biradicals. Ab Initio Calculations of the Structures, Thermochemical Properties, and Singlet−Triplet Splittings of the Didehydronaphthalenes

Robert R. Squires and Christopher J. Cramer

J. Phys. Chem. A, 1998, 102, 9072
DOI: 10.1021/jp983449b

On the aromaticity and stability of benzynes in the ground and lowest‐lying triplet excited states

Rodrigo Báez‐Grez and Ricardo Pino‐Rios

J Comput Chem, 2024, 45, 6
DOI: 10.1002/jcc.27214

A Curtin–Hammett pentamethylene chain symmetrization process in the Bergman cyclization of an 11‐membered ring enediyne

Edyta M. Greer, Christopher V. Cosgriff and Olga Lavinda

J of Physical Organic Chem, 2012, 25, 1293
DOI: 10.1002/poc.3018

Computer Design of Anticancer Drugs. A New Enediyne Warhead

Elfi Kraka and Dieter Cremer

J. Am. Chem. Soc., 2000, 122, 8245
DOI: 10.1021/ja001017k

100 Jahre Didehydroaromaten

Hans Henning Wenk, Michael Winkler and Wolfram Sander

Angewandte Chemie, 2003, 115, 518
DOI: 10.1002/ange.200390119

Bis(enediyne) Macrocycles: Synthesis, Reactivity, and Structural Analysis

Heather S Blanchette, Stephen C Brand, Hitoshi Naruse, Timothy J.R Weakley and Michael M Haley

Tetrahedron, 2000, 56, 9581
DOI: 10.1016/S0040-4020(00)00932-7

Magnetic Properties and Aromaticity ofo-,m-, andp-Benzyne

Frank De Proft, Paul von Ragué Schleyer, Joop H. van Lenthe, Frank Stahl and Paul Geerlings

Chem. Eur. J., 2002, 8, 3402
DOI: 10.1002/1521-3765(20020802)8:15<3402::AID-CHEM3402>3.0.CO;2-6

Alkynyl Crown Ethers as a Scaffold for Hyperconjugative Assistance in Noncatalyzed Azide–Alkyne Click Reactions: Ion Sensing through Enhanced Transition-State Stabilization

Brian Gold, Paratchata Batsomboon, Gregory B. Dudley and Igor V. Alabugin

J. Org. Chem., 2014, 79, 6221
DOI: 10.1021/jo500958n

Biosynthesis and function of polyacetylenes and allied natural products

Robert E. Minto and Brenda J. Blacklock

Progress in Lipid Research, 2008, 47, 233
DOI: 10.1016/j.plipres.2008.02.002

Nucleophilic Addition of Enolates to 1,4-Dehydrobenzene Diradicals Derived from Enediynes: Synthesis of Functionalized Aromatics

Annadka Shrinidhi and Charles L. Perrin

ACS Omega, 2022, 7, 22930
DOI: 10.1021/acsomega.2c02916

One Century of Aryne Chemistry

Hans Henning Wenk, Michael Winkler and Wolfram Sander

Angew Chem Int Ed, 2003, 42, 502
DOI: 10.1002/anie.200390151

An Extended Multireference Study of the Singlet and Triplet States of the 9,10-didehydroanthracene Diradical

Hui Hu, Boyi Zhang, Adam Luxon, Thais Scott, Baoshan Wang and Carol A. Parish

J. Phys. Chem. A, 2018, 122, 3688
DOI: 10.1021/acs.jpca.8b01233

Reactivity of 1,4-didehydronaphthalene toward organic hydrogen atom donors

Kami K Thoen, Jason C Thoen and Fatih M Uckun

Tetrahedron Letters, 2000, 41, 4019
DOI: 10.1016/S0040-4039(00)00575-X

Electrophilic Cyclization of Aryldiacetylenes in the Synthesis of Functionalized Enediynes Fused to a Heterocyclic Core

N. A. Danilkina, A. E. Kulyashova, A. F. Khlebnikov, S. Bräse and I. A. Balova

J. Org. Chem., 2014, 79, 9018
DOI: 10.1021/jo501396s

Performance of the hybrid density functionals in the determination of the geometric structure, vibrational frequency and singlet–triplet energy separation of CH2, CHF, CF2, CCl2 and CBr2

D Das and S.L Whittenburg

Journal of Molecular Structure: THEOCHEM, 1999, 492, 175
DOI: 10.1016/S0166-1280(99)00169-4

The Structure ofmeta-Benzyne RevisitedA Close Look into σ-Bond Formation

Michael Winkler and Wolfram Sander

J. Phys. Chem. A, 2001, 105, 10422
DOI: 10.1021/jp012100c

ChemInform Abstract: Cyclic Enediynes: Relationship Between Ring Size, Alkyne Carbon Distance, and Cyclization Barrier.

P. R. SCHREINER

ChemInform, 1998, 29
DOI: 10.1002/chin.199823021

Bergman, Aza-Bergman, and Protonated Aza-Bergman Cyclizations and Intermediate 2,5-Arynes: Chemistry and Challenges to Computation

Christopher J. Cramer

J. Am. Chem. Soc., 1998, 120, 6261
DOI: 10.1021/ja9806579