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Volumn 44, Issue 5, 1997, Pages 477-493

Synthetic Approach Towards Hexaprismane. A Novel Entry to Homosecohexaprismane Skeleton by Cage Enlargement

Author keywords

Cage compounds; Diels Alder reaction; Fragmentation; Hexaprismane; Homoseco hexaprismane; Photocyclization

Indexed keywords


EID: 0346542477     PISSN: 00094536     EISSN: None     Source Type: Journal    
DOI: 10.1002/jccs.199700073     Document Type: Article
Times cited : (11)

References (69)
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    • For recent reviews on [n]-prismanes, see: (a) Mehta, G. in Strain and Its Implications in Organic Chemistry de Meijere, A.; Blechert, S., Eds. Kluwer Academic Publishers: Dordrecht, 1989, pp 269-281. (b) Mehta, G.; Padma, S. in Carbocyclic Cage Compounds: Chemistry and Applications, Osawa, E.; Yonemitsu, O., Eds. VCH: Weinheim, Germany, 1992, pp 183-215. (c) Forman, M. A.; Dailey, W. P. Org. Prep. & Proc. Int. 1994, 26, 291.
    • (1992) Carbocyclic Cage Compounds: Chemistry and Applications , pp. 183-215
    • Mehta, G.1    Padma, S.2
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    • For recent reviews on [n]-prismanes, see: (a) Mehta, G. in Strain and Its Implications in Organic Chemistry de Meijere, A.; Blechert, S., Eds. Kluwer Academic Publishers: Dordrecht, 1989, pp 269-281. (b) Mehta, G.; Padma, S. in Carbocyclic Cage Compounds: Chemistry and Applications, Osawa, E.; Yonemitsu, O., Eds. VCH: Weinheim, Germany, 1992, pp 183-215. (c) Forman, M. A.; Dailey, W. P. Org. Prep. & Proc. Int. 1994, 26, 291.
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    • For examples of unsuccessful attempts at the synthesis of [n]-prismanes and related systems via [2+2] photocyclization of a cis-divinylcyclobutane derivative, see: (a) McKennis, J. S.; Brener, L.; Ward, J. S.; Petit, R. J. Am. Chem. Soc. 1971, 93, 4957. (b) Raquette, L. A.; Davis, R. F.; James, D. R. Tetrahedron Lett. 1974, 1615. (c) Marchand, A. P.; Arney, Jr., B. E.; Gilardi, R.; Flippen- Anderson, J. L. J. Org. Chem. 1987, 52, 3455. (d) Marchand, A. P.; Rajapaksa, D.; Vidyasagar, V.; Eckrich, R.; Kumar, K. A. Tetrahedron 1995, 51, 11937. (e) Ref. 7(b).
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    • For examples of unsuccessful attempts at the synthesis of [n]-prismanes and related systems via [2+2] photocyclization of a cis-divinylcyclobutane derivative, see: (a) McKennis, J. S.; Brener, L.; Ward, J. S.; Petit, R. J. Am. Chem. Soc. 1971, 93, 4957. (b) Raquette, L. A.; Davis, R. F.; James, D. R. Tetrahedron Lett. 1974, 1615. (c) Marchand, A. P.; Arney, Jr., B. E.; Gilardi, R.; Flippen-Anderson, J. L. J. Org. Chem. 1987, 52, 3455. (d) Marchand, A. P.; Rajapaksa, D.; Vidyasagar, V.; Eckrich, R.; Kumar, K. A. Tetrahedron 1995, 51, 11937. (e) Ref. 7(b).
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    • For examples of unsuccessful attempts at the synthesis of [n]-prismanes and related systems via [2+2] photocyclization of a cis-divinylcyclobutane derivative, see: (a) McKennis, J. S.; Brener, L.; Ward, J. S.; Petit, R. J. Am. Chem. Soc. 1971, 93, 4957. (b) Raquette, L. A.; Davis, R. F.; James, D. R. Tetrahedron Lett. 1974, 1615. (c) Marchand, A. P.; Arney, Jr., B. E.; Gilardi, R.; Flippen- Anderson, J. L. J. Org. Chem. 1987, 52, 3455. (d) Marchand, A. P.; Rajapaksa, D.; Vidyasagar, V.; Eckrich, R.; Kumar, K. A. Tetrahedron 1995, 51, 11937. (e) Ref. 7(b).
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    • Ref. 7(b)
    • For examples of unsuccessful attempts at the synthesis of [n]-prismanes and related systems via [2+2] photocyclization of a cis-divinylcyclobutane derivative, see: (a) McKennis, J. S.; Brener, L.; Ward, J. S.; Petit, R. J. Am. Chem. Soc. 1971, 93, 4957. (b) Raquette, L. A.; Davis, R. F.; James, D. R. Tetrahedron Lett. 1974, 1615. (c) Marchand, A. P.; Arney, Jr., B. E.; Gilardi, R.; Flippen- Anderson, J. L. J. Org. Chem. 1987, 52, 3455. (d) Marchand, A. P.; Rajapaksa, D.; Vidyasagar, V.; Eckrich, R.; Kumar, K. A. Tetrahedron 1995, 51, 11937. (e) Ref. 7(b).
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    • and references cited therein
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    • note
    • Taken in part from the theses presented by G.-H. Lin in June 1996, and Y.-L. Yeh in June 1995, to the Chung Cheng University, in partial fulfillment of the requirements for the degree of Master of Science.
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    • note
    • 2/THF, reflux) to furnish enediol 26.
  • 56
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    • note
    • We do not think that abstraction of hydrogen atoms from the two hydroxyl groups of an 1,4-diol would occur concurrently to form a bis-alkoxy radical and as an intermediate in the fragmentation reaction. The statement here is only for the purpose of simple description of the overall resulting picture.
  • 64
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    • (b) Tori, K.; Hata, Y.; Muneyuki, R.; Takano, Y.; Tsuji, T.; Tanida, H. Can. J. Chem. 1964, 42, 926. The chemical shift of olefinic protons in cyclobutene (δ 5.95) verses that of norbomene (δ 5.98) might suggest that this pure fragmentation product is 34 and not 33.
    • (1964) Can. J. Chem. , vol.42 , pp. 926
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    • Ref. 35a, p 221
    • Ref. 35a, p 221.
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    • The atomic coordinates, bond lengths, and bond angles for this structure have been deposited at Cambridge Crystallographic Data Center
    • The atomic coordinates, bond lengths, and bond angles for this structure have been deposited at Cambridge Crystallographic Data Center.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.