ChemInform Abstract: Photochemical Addition of Methanol to Stilbenes.

Abstract

The photochemical addition of methanol (II) to stilbene (I) involves two competitive pathways: direct addition of methanol to the alkenic bond or insertion of a carbene (VI), emerging from a 1,2‐H shift in (I) to methanol.

Photochemical addition of methanol to stilbenes

“…The reaction depicted in Scheme 1 has been performed successfully with several stilbene derivatives, e.g. 1,2-diphenylcyclopentene (2), 3-phenyl-1,2-dihydronaphthalene, 14 Scheme 2, R' = R2 = F]. In case of the asymmetrically substituted 4-methoxy-(8a) and 4-methoxy-4'-methylstilbene (8b) addition of MeOH was observed to occur regioselectively, affording the methanol adducts (10a) and (lob) respectively, in accordance with Markovnikov's rule (Scheme 2).…”

“…1 -Methoxy-1,2-diphenylethane (4). Authentic (4) was prepared from 1,2-diphenylethanol in 70% yield;', 6(90 MHz; CDCl,) 2.76-3.23 [2 H, m (AB of ABX), J2,,, 13.68 Hz, 2-H and 2-H'], OCH,), 4.32 (1 H, t, 1-H), and 7.08 -32(MeOH)], 220 (14), 175 (30), 147 (18), 145 (18), 143 (30), 117 (72), and 91 (13).…”