2,3‐Dihydro‐1H‐naphtho[1,8‐cd]borinine as a Potent Precursor for Open‐Shell Singlet B‐Heterocycles

Abstract

The reaction of naphthalene-1,8-diylbis[(trimethylsilyl)methanide] and dimethyl arylboronates afforded the corresponding 2,3-dihydro-1H-naphtho [1,8-cd]borinine as single dia- [a]

Photoinduced boron atom insertion of benzocyclobutene forming an unprecedented fused boron heterocyclic radical

“…The C-B bond lengths of species B are 1.535 Å and 1.543 Å, which is close to the 1.552 Å and 1.561 Å that were determined by X-ray crystallography. 14 A comparison of the calculated vibrational frequencies, intensities, and boron isotopic shifts with experimental observations are shown in Table 1, which are in excellent agreement. For species A, the observed 1544.8 cm À1 absorption is predicted at 1561.3 cm À1 without a boron isotopic shift.…”

“…The C–B bond lengths of species B are 1.535 Å and 1.543 Å, which is close to the 1.552 Å and 1.561 Å that were determined by X-ray crystallography. 14…”

Sequential condensation and double desulfonylative cyclopropanation of 1,2-bis(sulfonylmethyl)arenes with 3-arylacroleins: access to biscyclopropane-fused tetralins

“…As shown in Scheme 4 and eqn (1), the desired 6an could not be detected via the tBuOK-mediated reaction of 4t with 5a, and only acenaphthylene was generated in 42% yield along with the removal of two molecules of sulfinic acid salts. 17 The plausible mechanism pathways could include (1) tBuOK-mediated benzylic deprotonation of 4t, (2) intramolecular desulfonylative annulation by the resulting carbanion A1, (3) deprotonation of the in situ formed G by tBuOK, (4) proton exchange from the generated carbanion H to I, and (5) desulfonylative transformation from I to acenaphthylene. The results showed that the carbanion A1 preferred to yield the acenaphthylene byproduct via intramolecular double self-desulfonylation such that the following intermolecular condensation and ring closure pathway were a The reactions were run at the 1.0 mmol scale with 4 and 5 (0.5 equiv.…”