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Exo- and endo-6-chlorobicyclo[3.1.0]hexanes

✍ Scribed by M.S. Baird; C.B. Reese

Publisher
Elsevier Science
Year
1967
Tongue
French
Weight
181 KB
Volume
8
Category
Article
ISSN
0040-4039

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✦ Synopsis

Reaction between cyclopentene and chlorocarbene (1) in ether solution at 20' gave exo--and endo-6-chlorobicyclo[j.l.O!hexanes (I and II, respectively), in ~a. 35% combined yields. The more abundant isomer (~a. 75% of the mixture) was isolated by preparative g.l.c., and characterized as a chlorocarbene adduct of cyclopentene by elemental analysis* and mass spectrometry; it had the following n.m.r. spectrum (in CC1 4 ): r6.72, triplet (J-7 c.p.s.1, weight 1, assigne4 to H(6); 'K7.8-8.5, comple.absorption, weight 8, assigned to all other protons. By virtue of the comparatively large coupling constant between H(6) and the other cyclopropyl protons (21, it was identified as the m-isomer (II). The chemical shift and splitting of H(6) correspond closely with the data reported for H(7) of endo-7-chlorobicyclo[4.l.O]heptane (3).

The less abundant exo-6-chlorobicyclo[3.1.Clhexane (I) could not be * Satisfactory analyses were obtained for all new compounds described.

πŸ“œ SIMILAR VOLUMES

Methyl exo-biΒ­cycloΒ­[3.1.0]Β­hexane-6,6-d
Methyl exo-biΒ­cycloΒ­[3.1.0]Β­hexane-6,6-diΒ­carboxylΒ­ate
✍ Yufit, Dmitrii S. ;Bagutskii, Viktor ;Howard, Judith A. K. ;Meijere, Armin de πŸ“‚ Article πŸ“… 2003 πŸ› International Union of Crystallography 🌐 English βš– 419 KB

The bicyclo[3.1.0]hexane fragment of the title molecule, C 9 H 12 O 4 , adopts a boat-like conformation, with its methoxycarbonyl substituent in the endo position. In the crystal structure, molecules form centrosymmetric OÐHÁ Á ÁO hydrogen-bonded dimers, which are arranged in layers.