Synthesis and Stereochemistry of Strained Naphthalenophanes

Abstract

We have studied the reaction of olefins (cyclopentene, cyclohexene, cycloheptene, and cyclooctene) with diethyl(methy1)silane ( I ) and carbon monoxide in the presence of C O~( C O )~. Instead of the products of type (2), expected by direct formal analogy with hydroformylation, the enol silyl ethers ( 3 ) were obtained. The yields were: ( 3 a ) 48 %, ( 3 b ) 71 %, ( 3 c ) 74 %, ( 3 d ) 69 %. Isomeric products were not formed. 0

A Cyclic Oligophenylene Containing Two 1,8-Naphthalene Units Bridged by Two Face-to-Face Biphenyl Linkages Exhibiting Unusual Strain and π−π Interaction

“…Although strained cyclophanes and oligophenylenes such as 1,2:9,10-dibenzo[2.2]paracyclophane-1,9-diene and naphthalenoparacyclophanes are known as π-acids and can be reduced chemically and electrochemically to produce the corresponding radical anions and dianions, , [3.3]paracyclophane behaves as a π-base to form the CT-complex with tetracyanoethylene (TCNE) in solution and in the solid state . The cyclic oligophenylene 2 , like [3.3]paracyclophane, forms CT-complexes with TCNE (λ max = 638 nm) and DDQ (λ max = 790 nm) in CH 2 Cl 2 .…”

The Radical Anions and Trianions of 1,8‐Diphenylnaphthalene and of Some of its Derivatives Containing a Cyclophane Substructure

“…~ Due to its peculiar geometry, 1,8-diphenylnaphthalene (1) [2] can be considered as embracing both naphthalene and cyclophane substructures. This description applies even more strictly to [2.0.0]( 1,4)benzeno( 1,8)naphthaleno( 1,4)benzenophane (3) and its monoene 4 [3] in which the para-positions of the Ph substituents of 1 are bridged by an ethano and an etheno group, respectively. In [ 11, we have recently reported the hyperfine data for the radical anion of 1, as well as for those of l,&bis(perdeuterio-pheny1)-(D,o-l) and 1,8-bis(p-tolyl)naphthalene (2).…”