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  2. Ketene cycloaddition - Wikipedia

    en.wikipedia.org/wiki/Ketene_cycloaddition

    Ketene cycloadditions proceed by a concerted, [2+2] cycloaddition mechanism. Ketenes, unlike most alkenes, can align antarafacially with respect to other alkenes. Thus, the suprafacial- antarafacial geometry required for concerted, thermal [2+2] cycloaddition can be achieved in reactions of ketenes. [4]

  3. Diborane - Wikipedia

    en.wikipedia.org/wiki/Diborane

    4 BCl 3 + 3 LiAlH 4 → 2 B 2 H 6 + 3 LiAlCl 4 4 BF 3 + 3 NaBH 4 → 2 B 2 H 6 + 3 NaBF 4. When heated with NaBH 4, tin(II) chloride is reduced to elemental tin, forming diborane in the process: SnCl 2 + 2NaBH 4 → 2NaCl + Sn + B 2 H 6 + H 2. Older methods entail the direct reaction of borohydride salts with a non-oxidizing acid, such as ...

  4. Ring-closing metathesis - Wikipedia

    en.wikipedia.org/wiki/Ring-closing_metathesis

    Without an additive, the reaction product is 2,3-dihydrofuran (2,3-DHF) and not the expected 2,5-dihydrofuran (2,5-DHF) together with the formation of ethylene gas. Radical scavengers, such as TEMPO or phenol, do not suppress isomerization; however, additives such as 1,4-benzoquinone or acetic acid successfully prevent unwanted isomerization.

  5. Borane–tetrahydrofuran - Wikipedia

    en.wikipedia.org/wiki/Borane–tetrahydrofuran

    [2] The complex can reduce carboxylic acids to alcohols and is a common route for the reduction of amino acids to amino alcohols [ 3 ] (e.g. valinol ). It adds across alkenes to give organoboron compounds that are useful intermediates. [ 4 ]

  6. Hydroboration - Wikipedia

    en.wikipedia.org/wiki/Hydroboration

    Hydroboration of 1,2-disubstituted alkenes, such as a cis or trans olefin, produces generally a mixture of the two organoboranes of comparable amounts, even if the steric properties of the substituents are very different. For such 1,2-disubstituted olefins, regioselectivity can be observed only when one of the two substituents is a phenyl ring.

  7. McMurry reaction - Wikipedia

    en.wikipedia.org/wiki/McMurry_reaction

    The reaction is named after its co-discoverer, John E. McMurry. The McMurry reaction originally involved the use of a mixture TiCl 3 and LiAlH 4, which produces the active reagents. Related species have been developed involving the combination of TiCl 3 or TiCl 4 with various other reducing agents, including potassium, zinc, and magnesium.

  8. Ammonia borane - Wikipedia

    en.wikipedia.org/wiki/Ammonia_borane

    Reaction of diborane with ammonia mainly gives the diammoniate salt [H 2 B(NH 3) 2] + [BH 4] − (diammoniodihydroboronium tetrahydroborate). Ammonia borane is the main product when an adduct of borane is employed in place of diborane: [5] BH 3 + NH 3 → BH 3 NH 3 + THF. It can also be synthesized from sodium borohydride. [6] [7] [8]

  9. Büchner–Curtius–Schlotterbeck reaction - Wikipedia

    en.wikipedia.org/wiki/Büchner–Curtius...

    The reaction is then completed either by the reformation of the carbonyl through an 1,2-rearrangement or by the formation of the epoxide. There are two possible carbonyl products: one formed by migration of R 1 (4) and the other by migration of R 2 (5). The relative yield of each possible carbonyl is determined by the migratory preferences of ...