Synthesis of anti-[1](1,6)Naphthaleno[1](1,6)naphthalenophane by Double Contractive Annulation of [2.2]Paracyclophane

Sourav Biswas; Zahra A Tabasi; Louise N Dawe; Yuming Zhao; Graham J Bodwell

doi:10.1021/acs.orglett.2c01602

Synthesis of anti-[1](1,6)Naphthaleno[1](1,6)naphthalenophane by Double Contractive Annulation of [2.2]Paracyclophane

Org Lett. 2022 Jul 22;24(28):5009-5013. doi: 10.1021/acs.orglett.2c01602. Epub 2022 Jul 10.

Authors

Sourav Biswas¹, Zahra A Tabasi¹, Louise N Dawe², Yuming Zhao¹, Graham J Bodwell¹

Affiliations

¹ Department of Chemistry, Memorial University of Newfoundland, 45 Arctic Avenue, St. John's, NL Canada, A1C 5S7.
² Department of Chemistry and Biochemistry, Wilfrid Laurier University, 75 University Avenue West, Waterloo, ON Canada, N2L 3C5.

PMID: 35815388
DOI: 10.1021/acs.orglett.2c01602

Abstract

Two-directional contractive annulation of [2.2]paracyclophane has led to the synthesis of anti-[1](1,6)naphthaleno[1](1,6)naphthalenophane (3). This [1.1]cyclophane (SE = 56.6 kcal/mol) consists of two bent and twisted naphthalene units with interplanar distances as short as 2.74 Å. Despite the high strain and structural distortion, 3 was found to be unreactive toward potential cycloaddition partners (TCNE, DMAD) and under UV irradiation.