Fully conjugated tetraborylethylene: selenium mediated C-C double bond formation from diborylcarbenoid.

ABSTRACT: Heteroatom-substituted ethylenes have long been studied owing to their potential application to electronic devices. In contrast to well-studied π-donor substituted ethylene, the π-acceptor substituted one has only been limitedly reported. While boron can be a candidate of π-acceptors, there has still been no example of fully conjugated tetraborylethylene (TBE). Herein, we synthesized the first fully conjugated TBE 2 by selenium-mediated C-C double bond formation from diborylcarbenoid 1, a synthetic equivalent of diborylcarbene (DBC). An intermediate of bis(diborylmethylene)-λ⁴-selane 3_Se, wherein two DBC fragments were bound to one selenium atom, was confirmed. TBE 2 has a longer C-C bond length of 1.368(2) Å than typical C-C double bonds (1.34 Å) owing to π-electron

SUBMITTER: Shibutani Y 

PROVIDER: S-EPMC11463700 | biostudies-literature | 2024 Oct

REPOSITORIES: biostudies-literature