New Friedel—Crafts Chemistry. XVI.¹ A Reconsideration of Cyclialkylation and Competing Reactions of Certain Phenylalkyl, Benzoylalkyl, and Acetylphenylalkyl Chlorides

Friedel-Crafts cyclialkylations of certain mono- and diphenyl-substituted alcohols and alkyl chlorides

“…(2), unidentified ( 18 15 (19), 24 (tr), cis-16 (11), irans-16 (70) 15 (19), 24 (tr), cis-16 (11), trans-16 (70) 15 (20), 24 (tr), cis-16 (9), trans-16 (71) Aids, petroleum ether' 10 20 57…”

Friedel–Crafts rearrangements. IV. Cyclialkylations and hydride transfers on phenylalkyl chlorides

“…The phenylalkyl chlorides required were prethese reactions so that Khalaf and Roberts have pared by decomposition of the chlorosulfite 1 reclassified the field as "new Friedel-Crafts esters of the alcohols or by the action of zinc I chemistry" (2). chloride -hydrochloric acid on the alcohols.…”

“…5) and ref. 2. The formation of naphthalene is indicative of a hydride transfer mechanism similar to that for cyclialkylation of 1 (Scheme 1).…”

Unexpected Rearrangements of Bicyclic Pyrazolines Derived from 6,6-Diphenylpentafulvene

“…Under the same reaction conditions, the minor regioisomeric pyrazolines 4 led quantitatively to a mixture of two rearrangement products: 1,3-diphenyl-5-[1-(3-phenylidenyl)methyl]pyrazoles 6 (70%) and 1,3,4-triaryl-4,9-dihydro-10H-4,9-methanobenzo [4,5]cyclohepta[1,2-c]pyrazoles 7 (30%). These structures (Scheme 3) have been established on the basis of their spectroscopic data and an X-ray study of 7c (Ar ϭ p-anisyl).…”

“…Molecular structure of compound 5b (Ar ϭ p-tolyl) in the crystal trophilic substitution on the neighbouring phenyl group. [3,4] The DQF-COSY [5,6] NMR spectrum of 5d ( Figure 2, Ar ϭ p-nitrophenyl) allowed us to identify each proton. This assignment has been generalised to all compounds 5.…”