Reaction of strained polycyclic ketones with diazomethane

Hirao, Kazuyuki; Kajikawa, Yoshimi; ABE, E.; Yonemitsu, Osamu

doi:10.1039/p19830001791

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1983

1993

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Cited by 7 publications

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“…This trapping process competes effectively with prototropic shift that would result in formation of an ylide-type structure that is capable of undergoing aldol condensation with unreacted starting material. 109 Hirao and co-workers109 also have investigated the reaction of 1,3-bishomocubanedione (258) with ethereal diazomethane (large excess) in the presence of methanol. Three products (261-263) were formed in this reaction in yields of 15%, 34%, and 15%, respectively.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and chemistry of homocubanes, bishomocubanes, and trishomocubanes

Marchand¹

1989

Chem. Rev.

147

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Section: Introductionmentioning

confidence: 99%

Synthesis and chemistry of homocubanes, bishomocubanes, and trishomocubanes

Marchand¹

1989

Chem. Rev.

147

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Functionalized Enantiomerically Pure [1.1.1]‐, [2.1.1]‐, [2.2.1]‐, and [2.2.2]Triblattanes

et al. 1993

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The methylene (2, 7, 10) and spirocyclopropane derivatives (8, 11, 12) are made accessible from rac-trishomocubane(mono-, di-, tri-)ones and optically pure unsaturated and benzoannulated [2.1.1]-(19, 48), [2.2.1]-(30, 53), and D3-symmetrical [2.2.2]triblattanes (3, 4) from the enantiomers of these ketones by expeditious (one pot) ring enlargement and olefination procedures. In the case of the central [2.2.2]trienes (+)-3/( -)-3, novel members of the (CH),, family, optical resolution is advantageously postponed to the stage of the intermediate [2.2.2]triones (35, 41) and effected via their (R,R)-2,3-butanediol acetals. In the a-diketone series only the [2.l.l]dione (70) is , and [2.2.2]Triblattanes 2277Demjanov procedure via 15/16r'71 or even 93% using the Schollkopf sequence via 13/14"'] was achieved. Scheme 2. i) N2HCC02Et/n-butyllithium/THF/-78 to -3 0 T / 97%.ii) C3H5Pd(I)C1 dimer/CH2Clz/-78 to room temp./96%. -iii) NaHC03/H20/150"C/1 h/100%.iv) TMSCN/Zn12/CH2C12. -v) LiAIHdTHF.vi) NaN02/H20/glacial acetic acid/iv-vi: 81 YO

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