The di-pi-methane rearrangement is a photochemical reaction of a molecular entity that contains two π-systems separated by a saturated carbon atom (a 1,4-diene or an allyl-substituted aromatic ring), to form an ene- (or aryl-) substituted cyclopropane. The rearrangement reaction formally amounts to a 1,2 shift of one ene group (in the diene) or the aryl group (in the allyl-aromatic analog) and bond formation between the lateral carbons of the non-migrating moiety.

Di-pi-methane rearrangement

Discovery & mechanism

This rearrangement was originally encountered in the photolysis of barrelene to give semibullvalene. Once the mechanism was recognized as general by Zimmerman in 1967, it was clear that the structural requirement was having two pi groups attached to an sp3-hybridized carbon, and then a variety of further examples was obtained. One was the photolysis of the Mariano Compound, 3,3-methyl-1,1,5,5-tetraphenyl-1,4-pentadiene. Another was the reaction of the Pratt diene

Equation 1. The mechanism of the Mariano diene rearranging

Equation 1. The mechanism of the Mariano diene rearranging

In contrast, in the case of the Pratt diene rearranging, there are two possible regiochemistries - a and b. Process a is preferred since it leaves benzhydryl odd-electron stabilization intact.

Equation 2. The mechanism of the Pratt diene rearranging; note the regioselectivity

Pratt Wiki.gif

The barrelene rearrangement is now presented. It is a bit more complex than the Mariano and Pratt examples since there are two sp3-hybridized (i.e. methane) carbons. Each such bridgehead carbon has three (ethylenic) pi bonds while two are needed for the di-pi-methane rearrangement. Another difference is that the barrelene reaction requires the triplet excited state while the Mariano and Pratt acyclic dienes used the excited singlet. Thus acetone is used in the barrelene reaction; acetone captures the light and then delivers triplet excitation to the barrelene reactant. In the final step of the rearrangement there is a spin-flip, termed intersystem-crossing (ISC) to provide paired electrons and a new sigma bond.

Equation 3. The mechanism of the Barrelene to Semibullvalene transformation

Barr to Semibullvalene Mech.gif

The dependence of the success of the Di-pi-Methane rearrangement on singlet versus triplet multiplicity arises primarily from the Free-Rotor Effect The triplet acyclic 1,4-dienes are free to undergo cis-trans interconversion of the diene double bonds (i.e. free-rotation) thus inhibiting the Di-pi-Methane process. The cis-trans isomerization proceeds by weakening of a pi-bond and then twisting. The singlet excited states don't rotate and then are free to undergo the Di-pi-Methane mechanism. For cyclic dienes, as in the barrelene example, the ring structure prevents cis-trans isomerization and the Di-pi-Methane can then occur.

References

  1. IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "di-π-methane rearrangement".
  2. Zimmerman, Howard E.; Armesto, Diego (1996). "Synthetic Aspects of the Di-π-methane Rearrangement". Chemical Reviews. 96 (8): 3065–3112. doi:10.1021/cr910109c. PMID 11848853.
  3. Zimmerman, H. E.; Grunewald, G. L. (1966). "The Chemistry of Barrelene. III. A Unique Photoisomerization to Semibullvalene". J. Am. Chem. Soc. 88 (1): 183–184. doi:10.1021/ja00953a045.
  4. Zimmerman, Howard E.; Binkley, Roger W.; Givens, Richard S.; Sherwin, Maynard A. (1967). Journal of the American Chemical Society. 89 (15): 3932. doi:10.1021/ja00991a064. Missing or empty |title= (help)
  5. Zimmerman, H. E.; Mariano, P. S (1969). "The Di-pi-Methane Rearrangement. Interaction of Electronically Excited Vinyl Chromophores". J. Am. Chem. Soc. 91: 1718–1727. doi:10.1021/ja01035a021.
  6. Hixson, Stephen S.; Mariano, Patrick S.; Zimmerman, Howard E. (1973). "Di-pi-methane and oxa-di-pi-methane rearrangements". Chemical Reviews. 73 (5): 531. doi:10.1021/cr60285a005.
  7. Zimmerman, H. E.; Pratt, A. C (1970). "Unsymmetrical Substitution and the Direction of the Di-pi-Methane Rearrangement; Mechanistic and Exploratory Organic Photochemistry. LVI". J. Am. Chem. Soc. 92: 6259–6267. doi:10.1021/ja00724a026.
  8. Zimmerman, H. E.; Schissel, D. N (1986). "Di-pi-Methane Rearrangement of Highly Sterically Congested Molecules; Inhibition of Free Rotor Energy Dissipation. Mechanistic and Exploratory Organic Photochemistry". J. Org. Chem. 51: 196–207. doi:10.1021/jo00352a013.

Di-pi-methane rearrangement

Deutsch Di-π-Methan-Umlagerung ▪ Українська Ди-π-метанове перегрупування

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Usually, the goods by request "Di-pi-methane rearrangement" in Texas can be delivered to the following cities: Houston, San Antonio, Dallas, Austin, Fort Worth, El Paso, Arlington, Corpus Christi, Plano, Laredo, Lubbock, Garland, Irving, Amarillo, Grand Prairie, Brownsville, McKinney, Frisco, Pasadena, Mesquite, Killeen, McAllen, Carrollton, Midland, Waco, Denton, Abilene, Odessa, Beaumont, Round Rock, The Woodlands, Richardson, Pearland, College Station, Wichita Falls, Lewisville, Tyler, San Angelo, League City, Allen, Sugar Land, Edinburg, Mission, Longview, Bryan, Pharr, Baytown, Missouri City, Temple, Flower Mound, New Braunfels, North Richland Hills, Conroe, Victoria, Cedar Park, Harlingen, Atascocita, Mansfield, Georgetown, San Marcos, Rowlett, Pflugerville, Port Arthur, Spring, Euless, DeSoto, Grapevine, Galveston...

Usually, the products related to the term "Di-pi-methane rearrangement" in Utah can be shipped to such cities as Salt Lake City, West Valley City, Provo, West Jordan, Orem, Sandy, Ogden, St. George, Layton, Taylorsville, South Jordan, Logan, Lehi, Murray, Bountiful, Draper, Riverton, Roy, Spanish Fork, Pleasant Grove, Cottonwood Heights, Tooele, Springville, Cedar City, Midvale. Delivery is also carried out in Kaysville, Holladay, American Fork, Clearfield, Syracuse, South Salt Lake, Herriman, Eagle Mountain, Clinton, Washington, Payson, Farmington, Brigham City, Saratoga Springs, North Ogden, South Ogden, North Salt Lake, Highland, Centerville, Hurricane, Heber City, West Haven, Lindon and smaller towns.

Of course, the products by request "Di-pi-methane rearrangement" in Vermont can be received in such cities as Burlington, South Burlington, Rutland, Barre, Montpelier, Winooski, St. Albans, Newport, Vergennes, etc.

It goes without saying that any products related with "Di-pi-methane rearrangement" in Virginia can be shipped to such cities as Virginia Beach, Norfolk, Chesapeake, Richmond, Newport News, Alexandria, Hampton, Roanoke, Portsmouth, Suffolk, Lynchburg, Harrisonburg, Charlottesville, Danville, Manassas, Petersburg, Fredericksburg, Winchester, Salem, Staunton, Fairfax, Hopewell, Waynesboro, Colonial Heights, Radford, Bristol, Manassas Park, Williamsburg, Falls Church, Martinsville, Poquoson, and other cities and towns.

As usual, the goods by request "Di-pi-methane rearrangement" in Washington can be received in Seattle, Spokane, Tacoma, Vancouver, Bellevue, Kent, Everett, Renton, Federal Way, Yakima, Spokane Valley, Kirkland, Bellingham, Kennewick, Auburn, Pasco, Marysville, Lakewood, Redmond, Shoreline, Richland, Sammamish, Burien, Olympia, Lacey. And other cities and towns, such as Edmonds, Puyallup, Bremerton, Lynnwood, Bothell, Longview, Issaquah, Wenatchee, Mount Vernon, University Place, Walla Walla, Pullman, Des Moines, Lake Stevens, SeaTac, Maple Valley, Mercer Island, Bainbridge Island, Oak Harbor, Kenmore, Moses Lake, Camas, Mukilteo, Mountlake Terrace, Tukwila...

And the products related to the term "Di-pi-methane rearrangement" in West Virginia can be received in Charleston, Huntington, Morgantown, Parkersburg, Wheeling, Weirton, Fairmont, Martinsburg, Beckley, Clarksburg, South Charleston, St. Albans, Vienna, Bluefield.

Today the found goods by query "Di-pi-methane rearrangement" in Wisconsin can be shipped to such cities as Milwaukee, Madison, Green Bay, Kenosha, Racine, Appleton, Waukesha, Oshkosh, Eau Claire, Janesville, West Allis, La Crosse, Sheboygan, Wauwatosa, Fond du Lac, New Berlin, Wausau. Delivery is also carried out in Brookfield, Beloit, Greenfield, Franklin, Oak Creek, Manitowoc, West Bend, Sun Prairie, Superior, Stevens Point, Neenah, Fitchburg, Muskego, Watertown, De Pere, Mequon, South Milwaukee, Marshfield.

As usual, the found goods by query "Di-pi-methane rearrangement" in Wyoming can be received in such cities as Cheyenne, Casper, Laramie, Gillette, Rock Springs, Sheridan, Green River, Evanston, Riverton, Jackson, Cody, Rawlins, Lander, Torrington, Powell, Douglas, Worland, and other cities.

Canada Delivery, Shipping to Canada

Naturally, any products related with "Di-pi-methane rearrangement" in Canada can be bought in Toronto, Montreal, Calgary, Ottawa, Edmonton, Mississauga, Winnipeg, Vancouver, Brampton, Hamilton, Quebec City, Surrey, Laval, Halifax, London, Markham, Vaughan, Gatineau, Longueuil, Burnaby, Saskatoon, Kitchener, Windsor, Regina, Richmond, Richmond Hill.

And also in Oakville, Burlington, Greater Sudbury, Sherbrooke, Oshawa, Saguenay, Lévis, Barrie, Abbotsford, St. Catharines, Trois-Rivières, Cambridge, Coquitlam, Kingston, Whitby, Guelph, Kelowna, Saanich, Ajax, Thunder Bay, Terrebonne, St. John's, Langley, Chatham-Kent, Delta.

And also in Waterloo, Cape Breton, Brantford, Strathcona County, Saint-Jean-sur-Richelieu, Red Deer, Pickering, Kamloops, Clarington, North Vancouver, Milton, Nanaimo, Lethbridge, Niagara Falls, Repentigny, Victoria, Newmarket, Brossard, Peterborough, Chilliwack, Maple Ridge, Sault Ste. Marie, Kawartha Lakes, Sarnia, Prince George.

The delivery is also available in Drummondville, Saint John, Moncton, Saint-Jérôme, New Westminster, Wood Buffalo, Granby, Norfolk County, St. Albert, Medicine Hat, Caledon, Halton Hills, Port Coquitlam, Fredericton, Grande Prairie, North Bay, Blainville, Saint-Hyacinthe, Aurora, Welland, Shawinigan, Dollard-des-Ormeaux, Belleville, North Vancouver, and other cities.

In fact, the products by request "Di-pi-methane rearrangement" can be shipped to any place in Canada, including Ontario, Quebec, British Columbia, Alberta, Manitoba, Saskatchewan, Nova Scotia, New Brunswick, Newfoundland and Labrador, and Prince Edward Island.

UK Delivery, Shipping to the United Kingdom

Normally, the goods by your query "Di-pi-methane rearrangement" in the United Kingdom can be delivered to the following cities: London, Birmingham, Leeds, Glasgow, Sheffield, Bradford, Edinburgh, Liverpool, Manchester, Bristol, Wakefield, Cardiff, Coventry, Nottingham, Leicester, Sunderland, Belfast, Newcastle upon Tyne, Brighton, Hull, Plymouth, Stoke-on-Trent.

It's also available for those who live in Wolverhampton, Derby, Swansea, Southampton, Salford, Aberdeen, Westminster, Portsmouth, York, Peterborough, Dundee, Lancaster, Oxford, Newport, Preston, St Albans, Norwich, Chester, Cambridge, Salisbury, Exeter, Gloucester. You can also buy these goods in Lisburn, Chichester, Winchester, Londonderry, Carlisle, Worcester, Bath, Durham, Lincoln, Hereford, Armagh, Inverness, Stirling, Canterbury, Lichfield, Newry, Ripon, Bangor, Truro, Ely, Wells, St. Davids, etc.

Actually, the goods related with "Di-pi-methane rearrangement" can be shipped to any place in the UK, including England, Scotland, Wales, and Northern Ireland.

Ireland Delivery, Shipping to Ireland

As you know, the goods by request "Di-pi-methane rearrangement" in Ireland can be purchased if you live in Dublin, Cork, Limerick, Galway, Waterford, Drogheda, Dundalk, Swords, Bray, Navan, Ennis, Kilkenny, Tralee, Carlow, Newbridge, Naas, Athlone, Portlaoise, Mullingar, Wexford, Balbriggan, Letterkenny, Celbridge, Sligo. And, of course, Clonmel, Greystones, Malahide, Leixlip, Carrigaline, Tullamore, Killarney, Arklow, Maynooth, Cobh, Castlebar, Midleton, Mallow, Ashbourne, Ballina, Laytown-Bettystown-Mornington, Enniscorthy, Wicklow, Tramore, Cavan, etc.

In fact, the goods by request "Di-pi-methane rearrangement" can be shipped to any place in Ireland, including Leinster, Ulster, Munster, and Connacht.

Australia Delivery, Shipping to Australia

No need to say, the found goods by query "Di-pi-methane rearrangement" in Australia can be received in such cities as Sydney, Melbourne, Brisbane, Perth, Adelaide, Gold Coast, Tweed Heads, Newcastle, Maitland, Canberra, Queanbeyan, Sunshine Coast, Wollongong, Hobart, Geelong, Townsville, Cairns, Darwin, Toowoomba, Ballarat, Bendigo, Albury, Wodonga, Launceston, Mackay.

It's also available for those who live in Rockhampton, Bunbury, Bundaberg, Coffs Harbour, Wagga Wagga, Hervey Bay, Mildura, Wentworth, Shepparton, Mooroopna, Gladstone, Tannum Sands, Port Macquarie, Tamworth, Traralgon, Morwell, Orange, Geraldton, Bowral, Mittagong, Dubbo, Busselton, Bathurst, Nowra, Bomaderry, Warrnambool, Albany, Warragul, Drouin, Kalgoorlie, Boulder, Devonport, and other cities.

In fact, the found goods by query "Di-pi-methane rearrangement" can be shipped to any place in Australia, including New South Wales, Victoria, Queensland, Western Australia, South Australia, Tasmania, Australian Capital Territory, and Northern Territory.

New Zealand Delivery, Shipping to New Zealand

As you know, the goods related with "Di-pi-methane rearrangement" in New Zealand can be delivered to the following cities: Auckland, Wellington, Christchurch, Hamilton, Tauranga, Napier-Hastings, Dunedin, Lower Hutt, Palmerston North, Nelson, Rotorua, New Plymouth, Whangarei, Invercargill, Whanganui, Gisborne, Porirua, Invercargill, Nelson, Upper Hutt, Gisborne, Blenheim, Pukekohe, Timaru, Taupo, and other cities and towns.

In other words, the goods by your query "Di-pi-methane rearrangement" can be shipped to any place in New Zealand, including North Island, South Island, Waiheke Island, and smaller islands. As usual,the products by requestcan be delivered to the following cities:As well as in, and other cities and towns.

In other words,
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