Linearly conjugated benzocyclohexadienone photochemistry in the solid state: Ionic chiral auxiliary mediated asymmetric induction

Tetrahedron Letters

Volumn 40, Issue 50, 1999, Pages 8737-8740

  Cheung, Eugene ^a   Netherton, Matthew R ^a   Scheffer, John R ^a   Trotter, James ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

Asymmetric induction; Ketones; Photochemistry; 2 a+ 2 a rearrangement

Indexed keywords

BENZOCYCLOHEXADIENONE DERIVATIVE; INORGANIC SALT; KETONE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CONFORMATIONAL TRANSITION; ENANTIOMER; HYDROGEN BOND; MOLECULAR MODEL; PHOTOCHEMISTRY; REACTION ANALYSIS; SOLID STATE;

EID: 0033544806     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01868-7     Document Type: Article

References (9)

1. See preceding three articles in this issue and references cited therein.
2. For a review of the photochemistry of linearly conjugated cyclohexadienones, see: (a) Schultz, A. G. In CRC Handbook of Organic Photochemistry and Photobiology; Horspool, W. M.; Song, P.-S., Eds.; CRC Press: Boca Raton, 1991; Chapter 58;
3. (b) Quinkert, G. Pure Appl. Chem. 1973, 33, 285.
4. The first paper in the present series of four articles also deals with the application of the solid state ionic auxiliary method of asymmetric synthesis to a conformationally rigid molecule.
5. 2O, 98%.
6. 1lc; a=10.874(2) Å, b=9.182(1) Å, c=11.247(2) Å; β=95.72°; Z=4; R=4.4%.
7. The gem-dimethyl groups are diastereotopic as a result of close contact between the chiral cation and achiral anion in the solvated ion pair.
8. 1; a=9.569(1) Å, b=14.204(4) Å, c=29.98(1) Å; Z=4; R=4.1%.
9. A similar situation has been observed for a salt that crystallizes in a disordered structure containing two differing conformations of the reacting species. See: Cheung, E.; Netherton, M. R.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1999, 121, 2919.