Carbenes generated within cyclodextrins and zeolites

Advances in Physical Organic Chemistry

Volumn 40, Issue , 2005, Pages 1-47

  Rosenberg, Murray G ^a   Brinker, Udo H ^a  

^a INSTITUT FÜR ORGANISCHE CHEMIE   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845934730     PISSN: 00653160     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0065-3160(05)40001-5     Document Type: Review

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243. Recently, diazirine rearrangement in the excited state (RIES) that mimics the result of cyclopropylcarbene fragmentation has been postulated. For examples, see: (a) Ref. 128d,e; (b) Thamattoor, D.M., Jones Jr., M., Pan, W. and Shevlin, P.B. (1996). Tetrahedron Lett. 37, 8333-8336
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259. The electron-deficient radical behaves similarly: (a) Davies, D.I., Done, J.N. and Hey, D.H. (1966). Chem. Commun. (London) 725-726; (b) Roberts, J.D., Trumbull Jr., E.R., Bennett, W. and Armstrong, R. (1950). J. Am. Chem. Soc. 72, 3116-3124
260. Carbocations stemming from carbenes can give deviant product ratios due to ion pairing (see Ref. 135a)
261. Carbocations stemming from diazonium cations, such as 57, often give spurious product ratios (see Ref. 84)
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263. Photolysis of 2-azi-5-norbornene (iso-45) is reported to give 55c:iso-55c=1.9. This ratio is slightly lower than usual for 58 and may also indicate some ion pairing: Kirmse, W. and Meinert, T. (1994). J. Chem. Soc., Chem. Commun. 1065-1066
264. The 55:iso-55 ratios obtained from carbenes 46 and iso-46 indicate a product spread in the direction of the starting compound: March, J. (ed.) (1992). Advanced Organic Chemistry (4th edn), p. 328. Wiley, New York
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267. One may postulate that H atom transfer to excited-state diazirine 45* leads to a diazene, 3-diazenylnortricyclane, that is responsible for the reduction
268. A carbonyl n→π* electronic transition (λ = ca. 280 nm) was observed with RP HPLC analysis, cf. Ref. 109
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277. The corresponding alkyne bicyclo[2.2.1]hept-2-yne might behave like a vic-dicarbene that first yields carbene 46 via 1,3-CH insertion, which then forms an intermolecular cyclopropanation product. However, this pathway was not suggested. See: (a) Laird, D.W. and Gilbert, J.C. (2001). J. Am. Chem. Soc. 123, 6704-6705; (b) Laird, D.W. and Gilbert, J.C. (2001). Chem. Eng. News 79 (28), 41
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283. -1 as calculated by Benson group additivity method: Benson, S.W., Cruickshank, F.R., Golden, D.M., Haugen, G.R., O'Neal, H.E., Rodgers, A.S., Shaw, R. and Walsh, R. (1969). Chem. Rev. 69, 279-324
284. Rearrangement in the excited state (RIES) of diazirine 45 might be the actual route to enyne 47 because MeOH, which is relatively reactive and in excess, is expected to trap carbene 46 completely
285. See Ref. 68g, pp. 137-159;
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296. No range is given in Ref. 160
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298. See Ref. 65
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