(1R*,4S*,10S*)-2,2,10-tribromo-1,2,3,4-tetrahydro-1,4-ethanonaphthalene

Ergin, Ömer; Harmandar, Mansur; Balci, M.

doi:10.1107/s0108270187090851

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“…Structures are known for two tribromides, viz. (1RS,4SR,10SR)-2,2,10-tribromo-1,2,3,4-tetrahydro-1,4-ethanonaphthalene, (IV) [Cambridge Structural Database (CSD;Allen, 2002) refcode FOMREE (Ergin et al, 1987)] (Scheme 2) and (1RS,3SR,4SR)-2,2,3-tribromo-1,2,3,4tetrahydro-1,4-ethanonaphthalene, (V) (refcode KAKVEZ; Eşsiz et al, 2011). Thus, (IV) lacks the Br atom at position 3, whilst (V) lacks that at position 10 compared with (I).…”

Section: Commentmentioning

confidence: 99%

A tetrabromo-1,4-ethanonaphthalene and related dibromo-1,4-ethenonaphthalene

Boeré

Bender

2013

Acta Crystallogr C

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(1RS,3RS,4RS,10SR)-2,2,3,10-Tetrabromo-1,2,3,4-tetrahydro-1,4-ethanonaphthalene, C12H10Br4, (I), is the first structure to be reported with four Br atoms bound to a 1,4-ethanonaphthalene framework and also the first which possesses three Br atoms in exo positions. Interactions between the Br atoms [three short intramolecular Br...Br distances of 3.1094 (4), 3.2669 (4) and 3.4415 (5) Å] have little effect on the C-C bond lengths but lead to significant twisting of the cage structure compared with the parent hydrocarbon, which is expected to be fully eclipsed at the two saturated C2H4 bridge positions. Chemically related (1SR,4RS)-2,3-dibromo-1,4-ethenonaphthalene, C12H8Br2, (II), obtained by double dehydrobromination of (I), represents the first structure of any halogen-substituted benzobarrelene. This cis-dibromide shows little evidence of steric congestion at the double bond [Br...Br = 3.5276 (8) Å] as a consequence of the large C-C-Br angles [average C=C-Br angle = 126.15 (10)°].

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Section: Commentmentioning

confidence: 99%